4269-17-4

Basic information

• Product Name: 4-Bromo-9H-fluoren-9-one
• Synonyms: NSC81339;4-broMo-9H-fluoren-9-one;4-Bromofluorenone;4-BroMo-9-fluorenone;4-Bromo-fluoren-9-one;9H-Fluoren-9-one, 4-bromo-;4-Bromo-9H-fluoren-9-one
• CAS NO: 4269-17-4
• Molecular Formula: C₁₃H₇BrO
• Molecular Weight: 259.09808
• Product Categories: OLED
• Mol File: 4269-17-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: 127.0 to 131.0 °C
• Boiling Point: 392.8°Cat760mmHg
• Flash Point: 131.3°C
• Appearance: /
• Density: 1.609
• Vapor Pressure: 2.23E-06mmHg at 25°C
• Refractive Index: 1.691
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-Bromo-9H-fluoren-9-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-9H-fluoren-9-one(4269-17-4)
• EPA Substance Registry System: 4-Bromo-9H-fluoren-9-one(4269-17-4)

Safety Data

• Hazardous Substances Data: 4269-17-4(Hazardous Substances Data)

Usage

General Description

4-Bromo-9H-fluoren-9-one, also known as 4-bromo-9-fluorenone, is an organic compound with the molecular formula C13H7BrO. It is a pale yellow solid that is commonly used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals, as well as a building block in the production of advanced materials. It is also known for its ability to undergo various organic reactions, such as halogenation, oxidation, and condensation, making it a versatile compound in organic chemistry. Additionally, it is a valuable research tool for the study of structure-activity relationships in organic compounds and the development of new synthetic methodologies.

InChI:InChI=1/C13H7BrO/c14-11-7-3-6-10-12(11)8-4-1-2-5-9(8)13(10)15/h1-7H

Synthetic route

bromobenzene (108-86-1) + 3-Bromopropionyl chloride (15486-96-1) → 4-bromo-9H-fluorene-9-one (4269-17-4)

Conditions	Yield
Stage #1: bromobenzene In dichloromethane at 5℃; for 0.5h; Stage #2: 3-Bromopropionyl chloride In dichloromethane at 5 - 20℃; for 16h; Stage #3: With trifluorormethanesulfonic acid In dichloromethane at 90℃; for 4h; Temperature; Reagent/catalyst;	88.5%

2'-bromo-[1,1'-biphenyl]-2-carbonitrile (54245-41-9) → 4-bromo-9H-fluorene-9-one (4269-17-4)

Conditions	Yield
With sulfuric acid; acetic acid for 12h; Reflux;	80%
With dichloro bis(acetonitrile) palladium(II); water; silver trifluoroacetate In N,N-dimethyl acetamide; trifluoroacetic acid at 140℃; for 72h; Heck Reaction; Glovebox; Inert atmosphere;	57%
With sulfuric acid

ethyl 2’-bromo-[1,1’-biphenyl]-2-carboxylate (690260-87-8) → 4-bromo-9H-fluorene-9-one (4269-17-4)

Conditions	Yield
With methanesulfonic acid at 100℃; for 14h;	61%

9-fluorenone (486-25-9) → 4-bromo-9H-fluorene-9-one (4269-17-4)

Conditions	Yield
With N-Bromosuccinimide; sulfuric acid In dichloromethane at 20℃; for 12h;	47.9%

1-Bromo-2-iodobenzene (583-55-1) + (S)-2-(3-bromo-2-iodophenyl)-4-isopropyl-4,5-dihydrooxazole → 4-bromo-9H-fluorene-9-one (4269-17-4) + (4S)-2-(6-bromo-2'-iodo-(1,1'-biphenyl)-2-yl)-4-isopropyl-4,5-dihydrooxazole

Conditions	Yield
Stage #1: (S)-2-(3-bromo-2-iodophenyl)-4-isopropyl-4,5-dihydrooxazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere; Stage #2: 1-Bromo-2-iodobenzene In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #3: With n-butyllithium In tetrahydrofuran; hexane at -78 - 25℃; for 12h; Inert atmosphere; diastereoselective reaction;	A 20% B 46%
Stage #1: (S)-2-(3-bromo-2-iodophenyl)-4-isopropyl-4,5-dihydrooxazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: 1-Bromo-2-iodobenzene In tetrahydrofuran; hexane at -78℃; for 12h; Overall yield = 46 %; Overall yield = 234 mg; diastereoselective reaction;	A n/a B n/a

furfural (98-01-1) + 2-bromo-2’-iodo-1,1’-biphenyl (39655-12-4) → 9-fluorenone (486-25-9) + 4-bromo-9H-fluorene-9-one (4269-17-4)

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 1,3-bis-(diphenylphosphino)propane; sodium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 48h; Inert atmosphere;	A 18% B 31%

4-bromo-9H-fluorene (19459-33-7) → 4-bromo-9H-fluorene-9-one (4269-17-4)

4-aminofluorenone (4269-15-2) → 4-bromo-9H-fluorene-9-one (4269-17-4)

Conditions	Yield
With hydrogen bromide Diazotization.Erhitzen mit CuBr und wss. HBr;

(2-amino-3-bromophenyl)(phenyl)methanone → 4-bromo-9H-fluorene-9-one (4269-17-4)

4-Brom-1-amino-fluorenon-(9) (16149-47-6) → 4-bromo-9H-fluorene-9-one (4269-17-4)

Conditions	Yield
(i) NaNO2, aq. HCl, (ii) H3PO2; Multistep reaction;

2'-bromo-biphenyl-carboxylic acid-(2) → 4-bromo-9H-fluorene-9-one (4269-17-4)

Conditions	Yield
With sulfuric acid at 45 - 50℃;

4-bromo-fluoren-9-ol (99514-93-9) → 4-bromo-9H-fluorene-9-one (4269-17-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; aqueous HI 2: acetic acid; Na2Cr2O7 View Scheme

1-Bromo-2-iodobenzene (583-55-1) → 4-bromo-9H-fluorene-9-one (4269-17-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: Cu 2: Py / dimethylformamide 3: aq. H2SO4 View Scheme

2,2'-dibromobiphenyl (13029-09-9) → 4-bromo-9H-fluorene-9-one (4269-17-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: Py / dimethylformamide 2: aq. H2SO4 View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: sulfuric acid / water / 2 h / 50 °C View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 18 h / -78 - 20 °C 2.1: sulfuric acid / 2 h / 0 - 50 °C View Scheme

1-amino-9H-fluoren-9-one (6344-62-3) → 4-bromo-9H-fluorene-9-one (4269-17-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: Br2, AcOH 2: (i) NaNO2, aq. HCl, (ii) H3PO2 View Scheme

2'-bromo-[1,1'-biphenyl]-2-carboxylic acid (69200-16-4) → 4-bromo-9H-fluorene-9-one (4269-17-4)

Conditions	Yield
With sulfuric acid In water at 50℃; for 2h;
With sulfuric acid at 0 - 50℃; for 2h;	36 g

1-Bromo-2-iodobenzene (583-55-1) + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → 4-bromo-9H-fluorene-9-one (4269-17-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: Pd(PPh3)2Cl2; tripotassium phosphate "n" hydrate / toluene / 12 h / 100 °C / Schlenk technique; Inert atmosphere 2: water; silver trifluoroacetate; dichloro bis(acetonitrile) palladium(II) / trifluoroacetic acid; N,N-dimethyl acetamide / 72 h / 140 °C / Glovebox; Inert atmosphere View Scheme

2-Cyanophenylboronic acid (138642-62-3) → 4-bromo-9H-fluorene-9-one (4269-17-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene / 2 h / 110 °C 2: Pd(PPh3)2Cl2; tripotassium phosphate "n" hydrate / toluene / 12 h / 100 °C / Schlenk technique; Inert atmosphere 3: water; silver trifluoroacetate; dichloro bis(acetonitrile) palladium(II) / trifluoroacetic acid; N,N-dimethyl acetamide / 72 h / 140 °C / Glovebox; Inert atmosphere View Scheme

methyl 2-iodo-3-bromobenzoate (121772-84-7) → 4-bromo-9H-fluorene-9-one (4269-17-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / Inert atmosphere 1.2: 0.33 h / Reflux 2.1: sodium hydroxide; ethanol / 6 h 3.1: methanesulfonic acid / 24 h / 30 °C View Scheme
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / Inert atmosphere 1.2: Reflux 2.1: sodium hydroxide / ethanol / 6 h / Reflux 3.1: methanesulfonic acid / 24 h / 30 °C View Scheme

phenylboronic acid (98-80-6) → 4-bromo-9H-fluorene-9-one (4269-17-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / Inert atmosphere 1.2: 0.33 h / Reflux 2.1: sodium hydroxide; ethanol / 6 h 3.1: methanesulfonic acid / 24 h / 30 °C View Scheme
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / Inert atmosphere 1.2: Reflux 2.1: sodium hydroxide / ethanol / 6 h / Reflux 3.1: methanesulfonic acid / 24 h / 30 °C View Scheme

C14H11BrO2 → 4-bromo-9H-fluorene-9-one (4269-17-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; ethanol / 6 h 2: methanesulfonic acid / 24 h / 30 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide / ethanol / 6 h / Reflux 2: methanesulfonic acid / 24 h / 30 °C View Scheme

6-bromo-biphenyl-2-carboxylic acid → 4-bromo-9H-fluorene-9-one (4269-17-4)

Conditions	Yield
With methanesulfonic acid at 30℃; for 24h;
With methanesulfonic acid at 30℃; for 24h;

4-bromo-9H-fluorene-9-one (4269-17-4) + phenylmagnesium bromide (100-58-3) → 2-bromo-9-phenyl-9H-fluoren-9-ol (736928-22-6)

Conditions	Yield
In tetrahydrofuran at 0℃; for 0.333333h;	100%

9-(2-bromophenyl)-9H-carbazole (902518-11-0) + 4-bromo-9H-fluorene-9-one (4269-17-4) → C31H18BrN

Conditions	Yield
Stage #1: 9-(2-bromophenyl)-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane at -78℃; for 3.67h; Stage #3: With sulfuric acid; acetic acid for 4h; Reflux;	97%
Stage #1: 9-(2-bromophenyl)-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane at -78 - 20℃; for 3.66667h;	97%
Stage #1: 9-(2-bromophenyl)-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane at -78 - 20℃; for 3.67h; Stage #3: With sulfuric acid; acetic acid for 4h; Reflux;	97%
Stage #1: 9-(2-bromophenyl)-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #3: With hydrogenchloride; acetic acid for 12h; Reflux;	65%

4-bromo-9H-fluorene-9-one (4269-17-4) → 2,4,7-tribromo-9H-fluoren-9-one

Conditions	Yield
With bromine In dichloromethane at 0 - 20℃; for 6h;	92%
With bromine In dichloromethane at 20℃; for 6h;	90%
With bromine In dichloromethane at 20℃; for 6h; Cooling with ice;	90%

4-bromo-9H-fluorene-9-one (4269-17-4) + 2,3-di-(4-tert-butylphenyl)-1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene → 4,4'-(4,4''-di-tert-butyl-[1,1':2',1''-terphenyl]-3',6'-diyl)bis(9H-fluoren-9-one)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium carbonate; XPhos In 1,4-dioxane; water at 100℃; for 24h; Suzuki Coupling; Schlenk technique; Sealed tube; Inert atmosphere;	91%

4-bromo-9H-fluorene-9-one (4269-17-4) + phenol (108-95-2) → 4-bromospiro[fluorene-9,9′-xanthene]

Conditions	Yield
With trichlorophosphate at 120℃;	87%
With trichlorophosphate

4-bromo-9H-fluorene-9-one (4269-17-4) + 1-(2-bromophenyl)naphthalene (18937-92-3) → C29H19BrO

Conditions	Yield
Stage #1: 1-(2-bromophenyl)naphthalene With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran at 20℃; Inert atmosphere; Stage #3: With water In tetrahydrofuran Inert atmosphere;	85.7%
Stage #1: 1-(2-bromophenyl)naphthalene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane at -78 - 20℃;	84%
Stage #1: 1-(2-bromophenyl)naphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran at -78 - 20℃; for 12h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water for 0.5h; Inert atmosphere;

4-bromo-9H-fluorene-9-one (4269-17-4) + 2-bromo-4,4’-dichloro-1,1’-biphenyl (179526-95-5) → C25H16BrClO

Conditions	Yield
Stage #1: 2-bromo-4,4’-dichloro-1,1’-biphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane at 20℃; for 1h;	85%

4-bromo-9H-fluorene-9-one (4269-17-4) + phenylboronic acid (98-80-6) → 4-phenyl-9H-fluoren-9-one (4269-14-1)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In N,N-dimethyl-formamide at 150℃; Suzuki-Miyaura Coupling; Inert atmosphere;	84%

4-bromo-9H-fluorene-9-one (4269-17-4) + 2-nitrophenylboronic acid (5570-19-4) → C19H11NO3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); bis(tri-t-butylphosphine)palladium(0); potassium carbonate In tetrahydrofuran; water for 2h; Reflux;	84%

9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (785051-54-9) + 4-bromo-9H-fluorene-9-one (4269-17-4) → 4-(4-(9Hcarbazol-9-yl)phenyl)-9H-fluoren-9-one

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;	82%

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1161009-89-7) + 4-bromo-9H-fluorene-9-one (4269-17-4) → 4-(9,9'-spirobifluorene-4-yl)-9H-fluoren-9-one (1257321-43-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water for 48h; Suzuki coupling; Reflux; Inert atmosphere;	81%

4-bromo-9H-fluorene-9-one (4269-17-4) + 2-(2-bromophenyl)dibenzo[b,e][1,4]dioxine → 4-bromo-9-(2-(dibenzo[b,e][1,4]dioxin-2-yl)phenyl)-9H-fluoren-9-ol

Conditions	Yield
Stage #1: 2-(2-bromophenyl)dibenzo[b,e][1,4]dioxine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran at 20℃; for 3h;	80%

4-bromo-9H-fluorene-9-one (4269-17-4) + 2,5-di-(4-tert-butylphenyl)-1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene → 4,4'-(4,4''-di-tert-butyl-[1,1':4',1''-terphenyl]-2',5'-diyl)bis(9H-fluoren-9-one)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium carbonate; XPhos In 1,4-dioxane; water at 100℃; for 24h; Suzuki Coupling; Schlenk technique; Sealed tube; Inert atmosphere;	79%

4-bromo-9H-fluorene-9-one (4269-17-4) + C18H11Br → C31H17Br

Conditions	Yield
Stage #1: C18H11Br With n-butyllithium In tetrahydrofuran; hexane at -78 - 70℃; for 0.5h; Inert atmosphere; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane for 1.5h; Inert atmosphere; Stage #3: With hydrogenchloride; acetic acid for 4h; Reflux;	78%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 4-bromo-9H-fluorene-9-one (4269-17-4) → 2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1161009-89-7)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 1h; Inert atmosphere;	77%

4-bromo-9H-fluorene-9-one (4269-17-4) + 1-(2-bromophenyl)naphthalene (18937-92-3) → C29H17Br

Conditions	Yield
Stage #1: 1-(2-bromophenyl)naphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran at 18 - 28℃; for 12h; Stage #3: With hydrogenchloride; acetic acid at 120℃; for 5h;	75%

4-bromo-9H-fluorene-9-one (4269-17-4) + N-(2-bromophenyl)-N-phenylbenzenamine (78600-31-4) → 4'-bromo-10-phenyl-10H-spiro[acridine-9,9'-fluorene]

Conditions	Yield
Stage #1: N-(2-bromophenyl)-N-phenylbenzenamine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Schlenk technique; Glovebox; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane at -78 - 25℃; for 21h; Inert atmosphere; Schlenk technique; Glovebox;	73%
Stage #1: N-(2-bromophenyl)-N-phenylbenzenamine With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Schlenk technique; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane at -78 - 20℃; for 13h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; Stage #3: With hydrogenchloride; acetic acid In water for 2h; Reflux;	56%
Stage #1: 4-bromo-9H-fluorene-9-one; N-(2-bromophenyl)-N-phenylbenzenamine With n-butyllithium In tetrahydrofuran Stage #2: With hydrogenchloride; acetic acid

4-bromo-9H-fluorene-9-one (4269-17-4) + 2-iodobiphenyl (2113-51-1) → C25H17BrO

Conditions	Yield
Stage #1: 2-iodobiphenyl With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran	73%

4-bromo-9H-fluorene-9-one (4269-17-4) + C36H26N4 → C49H32N4O

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium t-butanolate In toluene for 14h; Inert atmosphere; Reflux;	73%

4-bromo-9H-fluorene-9-one (4269-17-4) + C18H11Br → C31H17Br

Conditions	Yield
Stage #1: C18H11Br With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 0.5h; Inert atmosphere; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane at -70 - 20℃; for 1.5h; Inert atmosphere; Stage #3: With hydrogenchloride; acetic acid In water for 4h; Reflux;	73%

9-(2-bromophenyl)-9H-carbazole (902518-11-0) + 4-bromo-9H-fluorene-9-one (4269-17-4) → C31H20BrNO

Conditions	Yield
Stage #1: 9-(2-bromophenyl)-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran at -78 - 20℃;	72%
With n-butyllithium In tetrahydrofuran at -78℃;

4-bromo-9H-fluorene-9-one (4269-17-4) + 10-(2-bromophenyl)-10H-phenoxazine (131013-62-2) → 4-bromooxacyclospirofluorenetriphenylamine

Conditions	Yield
Stage #1: 10-(2-bromophenyl)-10H-phenoxazine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran at -78 - 20℃; for 13h; Inert atmosphere;	70%
Stage #1: 10-(2-bromophenyl)-10H-phenoxazine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #3: With hydrogenchloride; acetic acid for 12h; Reflux;	62%

4-bromo-9H-fluorene-9-one (4269-17-4) + 1-(2-bromophenoxy)naphthalene → 4-bromo-9-(2-(naphthalen-1-yloxy)phenyl)-9H-fluoren-9-ol

Conditions	Yield
Stage #1: 1-(2-bromophenoxy)naphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 3.5h; Inert atmosphere; Stage #2: 4-bromo-9H-fluorene-9-one With n-butyllithium In tetrahydrofuran for 12h; Inert atmosphere;	67%

4-bromo-9H-fluorene-9-one (4269-17-4) + C18H13Br → C31H19Br

Conditions	Yield
Stage #1: C18H13Br With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 0.5h; Inert atmosphere; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane at -70 - 20℃; for 1.5h; Inert atmosphere; Stage #3: With hydrogenchloride; acetic acid In water for 4h; Reflux;	66%

4-bromo-9H-fluorene-9-one (4269-17-4) + 4-(2-bromophenyl)-dibenzothiophene (143546-42-3) → C31H17BrS

Conditions	Yield
Stage #1: 4-(2-bromophenyl)-dibenzothiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran; hexane at 20℃; Stage #3: With hydrogenchloride In ethanol at 75℃;	65%

4-bromo-9H-fluorene-9-one (4269-17-4) + 2-bromo-3-phenylfuran → 4-bromospiro[fluorene-9,8'-indeno[2,1-b]furan]

Conditions	Yield
Stage #1: 2-bromo-3-phenylfuran With magnesium In tetrahydrofuran at 40℃; for 1h; Inert atmosphere; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran for 5h; Reflux; Inert atmosphere;	55.1%

4-bromo-9H-fluorene-9-one (4269-17-4) + 4-N,N-diphenylamino-1-bromobenzene (36809-26-4) → C31H22BrO2P

Conditions	Yield
Stage #1: 4-N,N-diphenylamino-1-bromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 4-bromo-9H-fluorene-9-one In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	50%

Upstream product

• 69200-16-4 2'-bromo-[1,1'-biphenyl]-2-carboxylic acid 
• 486-25-9 9-fluorenone 
• 108-86-1 bromobenzene 
• 15486-96-1 3-Bromopropionyl chloride 
• 690260-87-8 ethyl 2’-bromo-[1,1’-biphenyl]-2-carboxylate 
• 98-80-6 phenylboronic acid 
• 121772-84-7 methyl 2-iodo-3-bromobenzoic acid 
• 583-55-1 1-Bromo-2-iodobenzene 
• 98-01-1 furfural 
• 39655-12-4 2-bromo-2’-iodo-1,1’-biphenyl 
• 138642-62-3 2-Cyanophenylboronic acid 
• 172732-52-4 o-cyanophenylboronic acid-1,3-propylene glycol ester 
• 6344-62-3 1-amino-9H-fluoren-9-one 
• 13029-09-9 2,2'-dibromobiphenyl 

Downstream Products

• 903-53-7 4-Brom-2,5,7-trinitro-fluorenon 
• 1257321-41-7 4,4’-dibromo-9,9’-spirobifluorene 
• 1161009-89-7 2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1374118-65-6 C₃₁H₁₈BrCl 
• 1161009-88-6 4-bromo-9,9’-spirobi[9H-fluorene] 
• 1598410-12-8 4'-bromo-10-phenyl-10H-spiro[acridine-9,9'-fluorene] 
• 1421789-05-0 (9,9'-spirobi[9H-fluoren]-4-yl)boronic acid 

Relevant articles and documents

Synthesis of Cyclopenta-HBCs and their Regioselective Chlorination During Oxidative Cyclodehydrogenation

Hexa-peri-hexabenzocoronenes with a bay-fused five-membered ring are synthesized from fluorenyl precursors. The key oxidative cyclodehydrogenation step is accompanied by regioselective chlorination that is enhanced by methylation at the cyclopenta-ring or increased reaction concentration. The CpHBC products undergo mild electrophilic aromatic bromination, without catalyst, to afford adducts suitable for π-extension by cross-coupling.

Intermediate 5 - bromine yinyin alkone preparation method (by machine translation)

The invention discloses an intermediate 5 - bromine yinyin alkone synthetic method, bromobenzene, dichloromethane, 3 - [...], concentrated hydrochloric acid, NaOH, 1 - tert-butyl 3 - methyl imidazole pressure concentrated water, double-(trifluoromethyl sulfonyl) imide as a main raw material, the process of the invention using the composite catalyst to avoid the corrosion of the equipment, the reaction conditions are easy to control, the yield is high, the product is easy to purification, and the reaction of the raw material 3 - chloropropionyl cheap and bromobenzene. To sum up, the preparation process have very good economic benefits can be the large-scale production. (by machine translation)

A containing 9, 9' - fluorene and dibenzofuran aromatic amine compound and its organic electroluminescent device (by machine translation)

The present invention provides a containing 9, 9' - fluorene and dibenzofuran aromatic amine compound and its organic electroluminescent light emitting device, relates to organic photoelectric material technical field. The compound preparation method is simple, easily available raw materials, has suitable the highest occupied molecular orbital energy level, high T1 value and high refractive index, and have very good hole transporting capability, thermal stability and film-forming properties, is applied to the OLED devices, can significantly improve the luminous efficiency of the device, heat resistance and service life, also can effectively reduce the driving voltage of the device. (by machine translation)