1878-68-8

Basic information

• Product Name: 4-Bromophenylacetic acid
• Synonyms: (p-bromophenyl)-aceticaci;4-bromo-benzeneaceticaci;4-Bromobenzeneaceticacid;4-Bromophenylacetic acid acid;Acetic acid, (p-bromophenyl)-;Aceticacid,(p-bromophenyl)-;Benzeneacetic acid, 4-bromo-;Benzeneaceticacid,4-bromo-(9CI)
• CAS NO: 1878-68-8
• Molecular Formula: C₈H₇BrO₂
• Molecular Weight: 215.04
• EINECS: 217-523-7
• Product Categories: Phenylacetic acid series;FINE Chemical & INTERMEDIATES;blocks;Bromides;Carboxes;Acids and Derivatives;Aromatic Phenylacetic Acids and Derivatives;Aromatics Compounds;Aromatics;C8;Carbonyl Compounds;Carboxylic Acids;carboxylic acid| alkyl bromide
• Mol File: 1878-68-8.mol
• Article Data: 24

Chemical Properties

• Melting Point: 114-117 °C(lit.)
• Boiling Point: 252.95°C (rough estimate)
• Flash Point: 151 °C
• Appearance: Almost white to light yellow-beige/Crystalline Powder
• Density: 1.5313 (rough estimate)
• Vapor Pressure: 9.03E-05mmHg at 25°C
• Refractive Index: 1.4620 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: ethanol: soluble5%, clear, colorless to light yellow
• PKA: pK1: 4.188 (25°C)
• Water Solubility: SLIGHTLY SOLUBLE
• BRN: 972146
• CAS DataBase Reference: 4-Bromophenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromophenylacetic acid(1878-68-8)
• EPA Substance Registry System: 4-Bromophenylacetic acid(1878-68-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 37/39-26-26/37/39-24/25
• WGK Germany: 3
• RTECS: AF6325000
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 1878-68-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

4-Bromophenylacetic acid was used as standard in the extraction of nonylphenol polyethoxy carboxylates with 1-4 ethoxy groups from sludge samples.

Biochem/physiol Actions

4-Bromophenylacetic acid is a growth inhibitory substance. It causes the depolarization effect on the transmembrane potential difference of tobacco protoplasts isolated from two genotypes differing in their sensitivity to auxins.

Purification Methods

The acid crystallises from H2O as needles. The acid chloride has b 238o/760mm, m 50o, and the anilide has m 174-175o. [Dippy & Williams J Chem Soc 161 1934, 1251 1948, Schwenk & Pala J Org Chem 11 798 1946, Beilstein 9 III 2275.]

InChI:InChI=1/C8H7BrO2/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4H,5H2,(H,10,11)/p-1

Synthetic route

4-bromo-DL-mandelic acid (6940-50-7) → 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With phosphonic Acid; methanesulfonic acid; sodium iodide In water at 95℃; for 72h; Inert atmosphere;	98.7%

(4-bromo-phenyl)-acetic acid methyl ester (41841-16-1) → 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With sodium hydroxide for 2h; Heating;	93%
With sodium hydroxide In tetrahydrofuran; methanol; water at 23℃; for 12h;

carbon monoxide (201230-82-2) + 1-bromomethyl-4-bromobenzene (589-15-1) → 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium iodide In formic acid at 60℃; under 760 Torr; for 18h; Carbonylation;	93%
With cobalt(II) pyridine-2-carboxylate; palladium diacetate; sodium hydroxide In methanol at 180℃; under 11251.1 Torr; for 6h; Autoclave;	93%

Ethyl 4-bromophenylacetate (14062-25-0) → 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With water; sodium hydroxide In 1,4-dioxane at 60℃; for 2h; pH=10 - 14;	93%

carbon dioxide (124-38-9) + hydrazone of p-bromobenzaldehyde (57477-93-7) → 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; caesium carbonate; cesium fluoride In N,N-dimethyl-formamide at 80℃; under 760.051 Torr; for 24h; chemoselective reaction;	88%

carbon monoxide (201230-82-2) + p-bromobenzyl chloride (589-17-3) → 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With cobalt(II) pyridine-2-carboxylate; palladium diacetate; sodium hydroxide In methanol at 180℃; under 11251.1 Torr; for 6h; Autoclave;	88%

methoxymethyl 2-(4-bromophenyl)acetate → 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With bismuth(III) chloride; water In acetonitrile at 50℃; for 1h;	85%

1-bromo-4-ethenyl-benzene (2039-82-9) → 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With Oxone; iodine In 1,2-dimethoxyethane; water at 20℃; for 4h; regioselective reaction;	83%
With D-glucose; oxygen In aq. phosphate buffer at 30℃; for 10h; pH=8; Green chemistry; Enzymatic reaction; regioselective reaction;	71%

carbon monoxide (201230-82-2) + 1-bromomethyl-4-bromobenzene (589-15-1) → para-bromotoluene (106-38-7) + 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With palladium hydroxide, 20 wt% on carbon; tetrabutylammomium bromide; water In tetrahydrofuran at 110℃; under 7500.75 Torr; for 4h; Sealed tube; Autoclave;	A 9 %Chromat. B 82%

cis-2,3-epoxy-3-(p-bromophenyl)propanenitrile → 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With boron trifluoride diethyl etherate; water In 1,4-dioxane at 175℃; for 0.5h; Microwave irradiation; Green chemistry;	78%

1,4-bromoiodobenzene (589-87-7) + acetic acid (64-19-7) → 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With silver(I) acetate; sodium acetate; palladium dichloride at 130℃; for 24h; Schlenk technique; Inert atmosphere; chemoselective reaction;	63%

2,2,2-trichloroethyl 2-(4-bromophenyl)acetate → 4-bromophenylacetic acid 2-deuterio-2,2-dichloroethyl ester (1255911-49-9) + 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With indium; deuterated ammonium chloride In tetrahydrofuran-d8; water-d2 at 20℃; for 40h; Reflux; chemoselective reaction;	A 3% B 54%

carbon monoxide (201230-82-2) + 1-bromomethyl-4-bromobenzene (589-15-1) → 4,4'-dibromobibenzyl (19829-56-2) + 1,3-bis(4-bromophenyl)propan-2-one (54523-47-6) + (4-Bromo-phenyl)-acetic acid 4-bromo-benzyl ester (88364-54-9) + 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
iron pentacarbonyl; tetrabutylammonium sulfate In sodium hydroxide; dichloromethane at 25℃; under 760 Torr; for 24h;	A 7% B 9% C 22% D 50%

carbon dioxide (124-38-9) + 2-[(4-bromophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (477841-90-0) → 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With potassium ethoxide In 1,4-dioxane at 100℃; for 24h;	50%

1-bromomethyl-4-bromobenzene (589-15-1) + /PBSAB018-1380/ → 4,4'-dibromobibenzyl (19829-56-2) + 1,3-bis(4-bromophenyl)propan-2-one (54523-47-6) + (4-Bromo-phenyl)-acetic acid 4-bromo-benzyl ester (88364-54-9) + 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With calcium hydroxide In dichloromethane; water at 20℃; for 23h;	A 5 % Spectr. B 62 % Spectr. C 11 % Spectr. D 4%

phenylacetic acid (103-82-2) → 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With water; bromine; mercury(II) oxide

phenylacetic acid (103-82-2) → ortho-bromophenylacetic acid (18698-97-0) + 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With bromine
With bromine; mercury(II) oxide
With water; bromine; mercury(II) oxide

4-Bromophenylacetonitrile (16532-79-9) → 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With sulfuric acid
With potassium hydroxide
With hydrogenchloride at 100℃; im Rohr;

4-aminophenylacetic acid (1197-55-3) → 2-(4-bromophenyl)-acetic acid (1878-68-8)

para-bromoacetophenone (99-90-1) → 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With morpholine; sulfur Erwaermen des Reaktionsprodukts mit aethanol. Natronlauge;
Multi-step reaction with 2 steps 1: BF3*O(C2H5)3, Pb(OAc)4 / benzene / 12 h / Ambient temperature 2: 93 percent / aq. NaOH / 2 h / Heating View Scheme
Stage #1: para-bromoacetophenone With morpholine; toluene-4-sulfonic acid; sulfur at 120℃; Stage #2: With tetrabutylammomium bromide; sodium hydroxide In ethanol; water at 100℃; for 4h;
Stage #1: para-bromoacetophenone With morpholine; toluene-4-sulfonic acid; sulfur at 120℃; Stage #2: With tetrabutylammomium bromide; sodium hydroxide at 100℃;

1-(2,2,2-trichloroethyl)-4-bromobenzene (65739-05-1) → 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With sulfuric acid
With sulfuric acid at 80 - 90℃; for 6h; Inert atmosphere;	117.4 g

phenacyl 4-bromophenylacetate → phenylacetic acid (103-82-2) + 2-oxo-2-phenylethyl 2-phenylacetate (98078-08-1) + acetophenone (98-86-2) + 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With N,N-dimethyl-aniline In acetonitrile for 2h; Mechanism; Irradiation; sensitized deprotection; competing bromide and carboxylate elimination;

phenylacetic acid (103-82-2) + water (7732-18-5) + bromine (7726-95-6) + mercury oxide → ortho-bromophenylacetic acid (18698-97-0) + 2-(4-bromophenyl)-acetic acid (1878-68-8)

phenylacetic acid (103-82-2) + N-Bromosuccinimide (128-08-5) + water (7732-18-5) → ortho-bromophenylacetic acid (18698-97-0) + benzaldehyde (100-52-7) + 2-(4-bromophenyl)-acetic acid (1878-68-8)

2-(4-bromophenyl)-1-morpholinoethanethione (77129-81-8) → 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride at 100℃; for 8h;

para-bromoacetophenone (99-90-1) + 12-phenylethynyl-6-methyl-5,6,7,12-tetrahydrodibenzo[c,f][1,5]azastibocine → 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: S; p-toluenesulfonic acid / 8 h / 120 - 130 °C 2: aq. NaOH; triethyl benzyl ammonium chloride / 8 h / 100 °C View Scheme

3-(4-bromo-phenyl)-2-thioxo-propionic acid (860190-07-4) → 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: aqueous ethanol; hydroxylamine 3: ethanolic KOH-solution View Scheme

3-(4-bromo-phenyl)-2-hydroxyimino-propionic acid (100246-20-6) → 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
Multi-step reaction with 2 steps 2: ethanolic KOH-solution View Scheme

benzyl chloride (100-44-7) → 2-(4-bromophenyl)-acetic acid (1878-68-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: Bromierung 2: ethanol 3: sulfuric acid View Scheme

2-(4-bromophenyl)-acetic acid (1878-68-8) → 2-(4-bromophenyl)acetyl chloride (37859-24-8)

Conditions	Yield
With thionyl chloride	100%
With thionyl chloride In dichloromethane	100%
With thionyl chloride In toluene	100%

methanol (67-56-1) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → (4-bromo-phenyl)-acetic acid methyl ester (41841-16-1)

Conditions	Yield
With chloro-trimethyl-silane for 15h; Ambient temperature;	100%
With hydrogenchloride for 1h; Heating;	100%
With hydrogenchloride for 3h; Heating;	100%

phenylboronic acid (98-80-6) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → (4-biphenylyl)acetic acid (5728-52-9)

Conditions	Yield
With sodium carbonate; Pd-complex on fluorous reversed silica gel In water at 80℃; for 16h; Suzuki reaction;	100%
With carbon-doped cobalt; C118H94N4O7P8; palladium diacetate; sodium carbonate In tetrahydrofuran; water at 20 - 60℃; for 14h; Suzuki Coupling; Inert atmosphere;	100%
With palladium diacetate; potassium carbonate In water; toluene at 65℃; for 20h; Solvent; Suzuki-Miyaura Coupling;	100%

4-fluoroboronic acid (1765-93-1) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → 2-(4'-fluoro-[1,1'-biphenyl]-4-yl)acetic acid (6908-38-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In toluene at 95℃; for 4h; Suzuki-Miyaura Coupling;	100%
With 2C2H5NO2*Pd(2+)*2Cl(1-); potassium carbonate In water at 20℃; for 6h; Suzuki-Miyaura Coupling; Green chemistry;	96%
With potassium carbonate In water at 20℃; for 4h; Suzuki-Miyaura Coupling; Green chemistry;	96%
Stage #1: 4-fluoroboronic acid; 2-(4-bromophenyl)-acetic acid With sodium carbonate; palladium 10% on activated carbon In water; isopropyl alcohol at 65 - 70℃; Suzuki Coupling; Stage #2: With sulfuric acid; water	75%

benzyl bromide (100-39-0) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → benzyl 2-(4-bromophenyl)acetate (127152-98-1)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20 - 100℃;	100%
With potassium carbonate In acetone for 12h; Reflux; Inert atmosphere;	95%
With potassium carbonate In N,N-dimethyl-formamide at 0 - 100℃; Inert atmosphere;	73%

4-aminotetrahydropyran (38041-19-9) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → 2-(4-bromophenyl)-N-(tetrahydropyran-4-yl)acetamide (1350411-40-3)

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 16h; Cooling with ice;	100%

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → 2-(4-bromophenyl)-N-(3,4-dimethoxyphenethyl)acetamide (109558-15-8)

Conditions	Yield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃;	100%
Stage #1: 2-(4-bromophenyl)-acetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.166667h; Stage #2: 2-(3,4-dimethoxyphenyl)-ethylamine With triethylamine In dichloromethane at 20℃;	90%

N-cyclohexyl-cyclohexanamine (101-83-7) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → C8H7BrO2*C12H23N

Conditions	Yield
In methanol at 20℃;	100%

2-(4-bromophenyl)-acetic acid (1878-68-8) → 4-bromophenethanol (4654-39-1)

Conditions	Yield
Stage #1: 2-(4-bromophenyl)-acetic acid With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 3h; Stage #2: With hydrogenchloride; water In tetrahydrofuran at 0 - 80℃; for 0.5h;	99%
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 0.25h;	92%
With C25H42N6Rh(1+)*CF3O3S(1-); phenylsilane In tetrahydrofuran at 30℃; for 20h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;	88%

5,6-dimethoxy-2-(N-propylamino)indan (162751-96-4) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → 2-(4-bromo-phenyl)-N-(5,6-dimethoxy-indan-2-yl)-N-propyl-acetamide (745062-37-7)

Conditions	Yield
With diethyl cyanophosphonate; triethylamine In dichloromethane at 20℃; for 24h;	99%

4-methoxyphenylboronic acid (5720-07-0) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → 2-(4'-methoxy-[1,1'-biphenyl]-4-yl)acetic acid (60277-22-7)

Conditions	Yield
With sodium carbonate; Pd-complex on fluorous reversed silica gel In water at 80℃; for 16h; Suzuki reaction;	99%
With potassium carbonate In water at 20℃; for 4h; Suzuki-Miyaura Coupling; Green chemistry;	97%
With 2C2H5NO2*Pd(2+)*2Cl(1-); potassium carbonate In water at 20℃; for 6h; Suzuki-Miyaura Coupling; Green chemistry;	92%
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In toluene at 95℃; for 4h; Suzuki-Miyaura Coupling;	52%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In methanol at 65℃; for 24h;

1-methyl-piperazine (109-01-3) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → 2-(4-bromophenyl)-1-(4-methylpiperazin-1-yl)ethan-1-one (349430-56-4)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 20h;	99%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 19h;	3.20 g

ethanol (64-17-5) + phenylboronic acid (98-80-6) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → 4-biphenylylacetic acid ethyl ester (14062-23-8)

Conditions	Yield
With tetra-butylammonium acetate; Pd EnCat-30TM In water at 120℃; for 0.166667h; Suzuki cross-coupling; microwave irradiation;	99%

6,7-dimethoxy-3-(4-methoxyphenyl)-1-(prop-2-en-1-yl)-1H-quinolin-2-one (874183-97-8) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → 4-{3-[1,2-dihydro-6,7-dimethoxy-3-(4-methoxyphenyl)-2-oxoquinolin-1-yl]prop-1-enyl}benzeneacetic acid

Conditions	Yield
With caesium carbonate; triphenylphosphine; [Pd(OAc)2] In water; N,N-dimethyl-formamide at 120℃; for 16h; Heck reaction;	99%

methyl iodide (74-88-4) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → (4-bromo-phenyl)-acetic acid methyl ester (41841-16-1)

Conditions	Yield
With potassium carbonate In acetone at 60℃;	99%
With potassium carbonate In acetone at 60℃;	99%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃; for 2h;	75%

2-(4-bromophenyl)-acetic acid (1878-68-8) → Ethyl 4-bromophenylacetate (14062-25-0)

Conditions	Yield
With sulfuric acid In ethanol	99%
With toluene-4-sulfonic acid In diethyl ether; ethanol
Multi-step reaction with 2 steps 1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 20 °C / Inert atmosphere 2: triethylamine; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere View Scheme

1-(tert-butoxycarbonyl)-4-aminopiperidine (87120-72-7) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → 4-[2-(4-bromophenyl)acetylamino]piperidine-1-carboxylic acid tert-butyl ester (1334001-49-8)

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	99%
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 1.25h;	96.9%
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 16h; Cooling with ice;	96.9%
Stage #1: 1-(tert-butoxycarbonyl)-4-aminopiperidine; 2-(4-bromophenyl)-acetic acid With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.0833333h; Stage #2: With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In dichloromethane at 20℃; for 3h;	93%

2-(4-bromophenyl)-acetic acid (1878-68-8) → 2-(4-bromo-phenyl)-3-hydroxy-propenal (885951-20-2)

Conditions	Yield
With trichlorophosphate In N,N-dimethyl-formamide at 4 - 75℃; for 16h; Inert atmosphere;	99%

trifluoroacetic acid (76-05-1) + 1-t-Butoxycarbonylpiperazine (57260-71-6) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → 2-(4-bromophenyl)-1-(piperazin-1-yl)ethanone trifluoroacetic acid

Conditions	Yield
Stage #1: 1-t-Butoxycarbonylpiperazine; 2-(4-bromophenyl)-acetic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Stage #2: trifluoroacetic acid In dichloromethane at 20℃; for 1h;	99%

1-t-Butoxycarbonylpiperazine (57260-71-6) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → C17H23BrN2O3 (1007210-75-4)

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;	98%

C7β-Hydroxyobacunone + 2-(4-bromophenyl)-acetic acid (1878-68-8) → C34H37BrO8

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	98%

α-bromocinnamaldehyde (5443-49-2) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → 4-bromo-2-(4-bromophenyl)-5-phenylpenta-2,4-dienoic acid

Conditions	Yield
With acetic anhydride; triethylamine for 5h; Knoevenagel Condensation; Reflux;	98%

C11H16ClN*ClH + 2-(4-bromophenyl)-acetic acid (1878-68-8) → C19H21BrClNO

Conditions	Yield
With triethylamine; 1,1'-carbonyldiimidazole In dichloromethane at 0 - 30℃;	98%

1-methyl-1-azaspiro<4.5>decan-10-amine (119878-15-8) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → 2-(4-Bromo-phenyl)-N-((5S,6R)-1-methyl-1-aza-spiro[4.5]dec-6-yl)-acetamide (119878-25-0)

Conditions	Yield
With 1,1'-carbonyldiimidazole In dichloromethane for 2h;	97%

ethanol (64-17-5) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → Ethyl 4-bromophenylacetate (14062-25-0)

Conditions	Yield
With sulfuric acid for 24h; Reflux;	97%
With toluene-4-sulfonic acid for 3h; Reflux;	97%
With toluene-4-sulfonic acid Inert atmosphere;	96%

2-(4-bromophenyl)-acetic acid (1878-68-8) → 2-(4-bromophenyl)acetic anhydride

Conditions	Yield
With dicyclohexyl-carbodiimide In toluene at 20℃; for 0.25h; Inert atmosphere;	97%
With 2,4,6-trimethyl-pyridine; bis(trichloromethyl) carbonate In tetrahydrofuran for 0.0166667h;
With dicyclohexyl-carbodiimide In toluene at 20℃; for 0.25h;

4-bromo-phenol (106-41-2) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → 4-bromophenyl 2-(4-bromophenyl)acetate (1017242-01-1)

Conditions	Yield
With dmap In dichloromethane at 0 - 20℃;	97%

N-(7-amino-1,8-naphthyridin-2-yl)-2-ethylhexanamide (1234564-83-0) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → N-(7-(2-(4-bromophenyl)acetamido)-1,8-naphthyridin-2-yl)-2-ethylhexanamide (1234564-87-4)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃; Inert atmosphere;	97%

3-trifluoromethylaniline (98-16-8) + 2-(4-bromophenyl)-acetic acid (1878-68-8) → 2-(4-bromo-phenyl)-N-(3-trifluoromethyl-phenyl)-acetamide (349420-02-6)

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h;	97%

Upstream product

• 99-90-1 para-bromoacetophenone 
• 41841-16-1 (4-bromo-phenyl)-acetic acid methyl ester 
• 65739-05-1 1-bromo-4-(2,2,2-trichloroethyl)benzene 
• 103-82-2 phenylacetic acid 
• 7732-18-5 water 
• 7726-95-6 bromine 
• 128-08-5 N-Bromosuccinimide 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 77129-81-8 2-(4-bromophenyl)-1-morpholinoethanethione 
• 2028-85-5 (4-bromophenyl)diazonium chloride 
• 106-41-2 4-bromo-phenol 
• 75-36-5 acetyl chloride 
• 106-38-7 para-bromotoluene 
• 14062-25-0 Ethyl 4-bromophenylacetate 

Downstream Products

• 3979-66-6 3-(4-bromobenzylidene)isobenzofuran-1-(3H)-one 
• 58922-30-8 1-bromo-4-((1E,3E)-4-phenylbuta-1,3-dien-1-yl)benzene 
• 37859-24-8 2-(4-bromophenyl)acetyl chloride 
• 85274-93-7 2-(4-bromophenyl)-N-phenylacetamide 
• 335205-31-7 2-(4-bromophenyl)-N-(p-tolyl)acetamide 
• 191999-28-7 (Z)-3-(4-bromobenzylidene)isobenzofuran-1(3H)-one 
• 16807-63-9 (E)-4-<2-(4-bromophenyl)ethenyl> phenol 
• 67205-73-6 2-(4-bromophenyl)-1-(4-methoxyphenyl)-1-ethanone 
• 19715-80-1 2-(4-bromophenyl)-N,N-dimethyl acetamide 
• 127152-98-1 benzyl 2-(4-bromophenyl)acetate 
• 41841-16-1 (4-bromo-phenyl)-acetic acid methyl ester 
• 106-49-0 p-toluidine 
• 14616-98-9 4-Brom-4'-chlor-stilben-α-carbonsaeure 
• 14335-71-8 4-Brom-stilben-α-carbonsaeure 

Relevant articles and documents

BiCl3-Facilitated removal of methoxymethyl-ether/ester derivatives and DFT study of -O-C-O- bond cleavage

A simple method for the cleavage of methoxymethyl (MOM)-ether and ester derivatives using bismuth trichloride (BiCl3) is described. The alkyl, alkenyl, alkynyl, benzyl and anthracene MOM ether derivatives, as well as MOM esters of both aliphatic and aromatic carboxylic acids, were deprotected in good yields. To better understand the molecular roles of BiCl3and water for MOM cleavage, two possible binding pathways were investigated using the density functional theory (DFT) method. The theoretical results indicate the differential initial binding site preferences of phenolic and alcoholic MOM substrates to the Bi atom and suggest that water plays a key role in facilitating the cleavage of the MOM group.

Method for converting benzyl borate compounds into phenylacetic acid and derivatives thereof by carbon dioxide

The invention discloses a method for converting benzyl borate compounds into phenylacetic acid and derivatives thereof by carbon dioxide. The method comprises the steps: dissolving the benzyl borate compounds and an alkali in an organic solvent in the absence of a metal catalyst, introducing carbon dioxide into the reaction system, carrying out a reaction at the temperature of 50-150 DEG C for 3-72 hours, and acidifying to obtain phenylacetic acid or the derivatives thereof. The method is a green, simple and efficient method for synthesizing phenylacetic acid and the derivatives thereof, greenhouse gas carbon dioxide is used as a carbon source in the reaction, no transition metal catalyst is used, and the method is environmentally friendly, economical and high in efficiency.

BF3·OEt2-promoted tandem Meinwald rearrangement and nucleophilic substitution of oxiranecarbonitriles

Tandem Meinwald rearrangement and nucleophilic substitution of oxiranenitriles was realized. Arylacetic acid derivatives were readily synthesized from 3-aryloxirane-2-carbonitriles with amines, alcohols, or water in the presence of boron trifluoride under microwave irradiation, and the designed synthetic strategy includes introducing a cyano leaving group into arylepoxides and capturing the in situ generated toxic cyanide with boron trifluoride, making the reaction efficient, safe, and environmentally benign. The reaction occurs through an acid-promoted Meinwald rearrangement, producing arylacetyl cyanides, followed by an addition-elimination process with nitrogen or oxygen-containing nucleophilic amines, alcohols or water. The current method provides a new application of the tandem Meinwald rearrangement.