o-<(6-bromo-1-naphthyl)methyl>acetophenone

Base Information

Chemical Name:o-<(6-bromo-1-naphthyl)methyl>acetophenone
CAS No.:86456-62-4
Molecular Formula:C₁₉H₁₅BrO
Molecular Weight:339.231
Hs Code.:

Synonyms:

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Chemical Property of o-<(6-bromo-1-naphthyl)methyl>acetophenone

Chemical Property:

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Technology Process of o-<(6-bromo-1-naphthyl)methyl>acetophenone

There total 14 articles about o-<(6-bromo-1-naphthyl)methyl>acetophenone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 20005-55-4
3-(4-bromophenyl)-1-butanol

: 86456-62-4
o-<(6-bromo-1-naphthyl)methyl>acetophenone

Guidance literature:: Multi-step reaction with 12 steps

1: 99 percent / triethylamine / CH₂Cl₂ / 1.) 0-5 deg C, 15 min, 2.) 2 h, 0-5 deg C

2: 93 percent / dicyclohexyl-18-crown-6 ether / acetonitrile / 1.) RT, 4 h, 2.) reflux, 2 h

3: 97.7 percent / KOH / H₂O; ethanol / 48 h

4: 75 percent / PPA / 2 h / 100 °C

5: NaBH₄ / methanol / 16 h / Ambient temperature

6: 81 percent / 1.) p-toluenesulfonic acid, 2.) chloranil / benzene / 1.) reflux, 2 h, 2.) reflux, 24 h

7: N-bromosuccinimide, benzoyl peroxide / CCl₄ / 6 h / Heating

8: 71 percent / 1.) hexamethylenetetramine, 2.) 50percent acetic acid / 1.) chloroform, reflux, 90 min, 2.) reflux, 90 min

9: n-butyllithium, conc. H₂SO₄

10: 88 percent / HI, H₃PO₂ / acetic acid; acetic anhydride / 5 h / Heating

11: thionyl chloride, DMF / CH₂Cl₂ / 18 h / Heating

12: cuprous iodide / 1.) -5 deg C, 25 min, ether

With potassium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; copper(l) iodide; n-butyllithium; thionyl chloride; Perbenzoic acid; hexamethylenetetramine; sulfuric acid; hydrogen iodide; hypophosphorous acid; chloranil; toluene-4-sulfonic acid; acetic acid; triethylamine; N,N-dimethyl-formamide; perhydrodibenzo-18-crown-6; In methanol; tetrachloromethane; ethanol; dichloromethane; water; acetic anhydride; acetic acid; acetonitrile; benzene;
DOI:10.1021/jo00165a029

Reference yield:

: 159755-11-0
1-bromo-4-(1-bromoethyl)benzene

: 86456-62-4
o-<(6-bromo-1-naphthyl)methyl>acetophenone

Guidance literature:: Multi-step reaction with 14 steps

1: dicyclohexyl-18-crown-6 ether / 1.) 0-5 deg C, 2.) 12 h, RT

2: borane-dimethyl sulfide

3: 99 percent / triethylamine / CH₂Cl₂ / 1.) 0-5 deg C, 15 min, 2.) 2 h, 0-5 deg C

4: 93 percent / dicyclohexyl-18-crown-6 ether / acetonitrile / 1.) RT, 4 h, 2.) reflux, 2 h

5: 97.7 percent / KOH / H₂O; ethanol / 48 h

6: 75 percent / PPA / 2 h / 100 °C

7: NaBH₄ / methanol / 16 h / Ambient temperature

8: 81 percent / 1.) p-toluenesulfonic acid, 2.) chloranil / benzene / 1.) reflux, 2 h, 2.) reflux, 24 h

9: N-bromosuccinimide, benzoyl peroxide / CCl₄ / 6 h / Heating

10: 71 percent / 1.) hexamethylenetetramine, 2.) 50percent acetic acid / 1.) chloroform, reflux, 90 min, 2.) reflux, 90 min

11: n-butyllithium, conc. H₂SO₄

12: 88 percent / HI, H₃PO₂ / acetic acid; acetic anhydride / 5 h / Heating

13: thionyl chloride, DMF / CH₂Cl₂ / 18 h / Heating

14: cuprous iodide / 1.) -5 deg C, 25 min, ether

With potassium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; copper(l) iodide; n-butyllithium; thionyl chloride; Perbenzoic acid; dimethylsulfide borane complex; hexamethylenetetramine; sulfuric acid; hydrogen iodide; hypophosphorous acid; chloranil; toluene-4-sulfonic acid; acetic acid; triethylamine; N,N-dimethyl-formamide; perhydrodibenzo-18-crown-6; In methanol; tetrachloromethane; ethanol; dichloromethane; water; acetic anhydride; acetic acid; acetonitrile; benzene;
DOI:10.1021/jo00165a029

Reference yield:

: 53086-46-7
3-(4-bromophenyl)butanoic acid

: 86456-62-4
o-<(6-bromo-1-naphthyl)methyl>acetophenone

Guidance literature:: Multi-step reaction with 13 steps

1: borane-dimethyl sulfide

2: 99 percent / triethylamine / CH₂Cl₂ / 1.) 0-5 deg C, 15 min, 2.) 2 h, 0-5 deg C

3: 93 percent / dicyclohexyl-18-crown-6 ether / acetonitrile / 1.) RT, 4 h, 2.) reflux, 2 h

4: 97.7 percent / KOH / H₂O; ethanol / 48 h

5: 75 percent / PPA / 2 h / 100 °C

6: NaBH₄ / methanol / 16 h / Ambient temperature

7: 81 percent / 1.) p-toluenesulfonic acid, 2.) chloranil / benzene / 1.) reflux, 2 h, 2.) reflux, 24 h

8: N-bromosuccinimide, benzoyl peroxide / CCl₄ / 6 h / Heating

9: 71 percent / 1.) hexamethylenetetramine, 2.) 50percent acetic acid / 1.) chloroform, reflux, 90 min, 2.) reflux, 90 min

10: n-butyllithium, conc. H₂SO₄

11: 88 percent / HI, H₃PO₂ / acetic acid; acetic anhydride / 5 h / Heating

12: thionyl chloride, DMF / CH₂Cl₂ / 18 h / Heating

13: cuprous iodide / 1.) -5 deg C, 25 min, ether

With potassium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; copper(l) iodide; n-butyllithium; thionyl chloride; Perbenzoic acid; dimethylsulfide borane complex; hexamethylenetetramine; sulfuric acid; hydrogen iodide; hypophosphorous acid; chloranil; toluene-4-sulfonic acid; acetic acid; triethylamine; N,N-dimethyl-formamide; perhydrodibenzo-18-crown-6; In methanol; tetrachloromethane; ethanol; dichloromethane; water; acetic anhydride; acetic acid; acetonitrile; benzene;
DOI:10.1021/jo00165a029