Bromine → 2-Bromo-1-(3,4-difluorophenyl)ethan-1-one

HRID 46555

Reaction equation

HRID 46555 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([F:11])[CH:5]=1)=[O:3].BrBr.ClC1C=C(Cl)C=CC=1C(=O)C[Br:19].C(C1C=CC=CC=1C(=O)CBr)C.C(C1C=CC(C(=O)CBr)=CC=1)(C)C.C(C1C=C(C=CC=1)C(=O)CBr)C(C)C.CC1C=C(C=CC=1C)C(=O)CBr.C(OC1C=C(C=CC=1)C(=O)CBr)C.C(OC1C=CC(C(=O)CBr)=CC=1)(C)C.C(OC1C=C(C=CC=1OCC)C(=O)CBr)C.FC1C=CC(F)=CC=1C(=O)CBr>C(Cl)(Cl)Cl.C(O)(=O)C>[F:11][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[F:10])[C:2](=[O:3])[CH2:1][Br:19]

Participants

14

Reactant 11

HCID 24408BromineHCID 758282-Bromo-1-(2,4-dichlorophenyl)ethan-1-oneHCID 1230521-(3,4-Difluorophenyl)ethan-1-oneHCID 27782642-Bromo-1-(2,5-difluorophenyl)ethanoneHCID 34921042-Bromo-1-(3,4-diethoxyphenyl)ethan-1-oneHCID 37031132-Bromo-1-(3,4-dimethylphenyl)ethan-1-oneHCID 140427562-Bromo-1-(4-(propan-2-yl)phenyl)ethan-1-oneHCID 154539122-Bromo-1-(4-(propan-2-yloxy)phenyl)ethan-1-oneHCID 20387511m-Isobutylphenacyl bromideHCID 226410062-Bromo-1-(3-ethoxyphenyl)ethanoneHCID 234426012-Bromo-1-(2-ethylphenyl)ethan-1-one

Product 1

HCID 27370322-Bromo-1-(3,4-difluorophenyl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 10.1 g. (0.065 mole) of 3,4-difluoroacetophenone in 100 ml. of glacial acetic acid was added 3.4 ml. (0.065 mole) of bromine dropwise. When the addition was complete the solution was stirred for 0.5 hr. and then stripped to dryness under reduced pressure. The residue was dissolved in chloroform and washed with aqueous sodium bicarbonate. Evaporation of the organic phase provided 14.8 g. (97%) of colorless liquid product. Similarly prepared were 2,4-dichlorophenacyl bromide, o-ethylphenacyl bromide, p-isopropylphenacyl bromide, m-isobutylphenacyl bromide, 3,4-dimethylphenacyl bromide, m-ethoxyphenacyl bromide, p-isopropoxyphenacyl bromide, 3,4-diethoxyphenacyl bromide, and 2,5-difluorophenacyl bromide.

Workup

  1. additionWhen the addition
  2. washwashed with aqueous sodium bicarbonate
  3. customEvaporation of the organic phase
  4. customprovided 14.8 g
  5. customSimilarly prepared

Sources & evidence

ORD record
ord-51ac15fa7aa84ece864078149c112857
Source dataset
uspto-grants-1979_11
Patent number
US04173650

Linked notes

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