Chloroform → Phenacyl bromide

HRID 2235058Notes

Reaction equation

HRID 2235058 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(Cl)(Cl)Cl.[Br:14]Br>C(OCC)C.C(Cl)Cl.C(O)(=O)C>[Br:14][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

7

Reactant 3

HCID 6212ChloroformHCID 7410Acetophenone3×HCID 24408Bromine2×

Product 1

HCID 6259Phenacyl bromide

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

The appropriate acetophenone (Intermediate A) was dissolved in diethyl ether, methylene chloride, or chloroform, and cooled to 0° C. Bromine (1.1 equiv) was dissolved in either methylenechloride or diethyl ether and added to the solution of acetophenone via a dropping funnel. After the addition of bromine was complete 2 drops of acetic acid were added and the solution was warmed to room temperature. Solvent was removed under reduced pressure to provide crude 2-bromoacetophenone (Intermediate B) which was generally used without further purification.

Workup

  1. additionwere added
  2. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-15aec3a9999e4c7da6c459d6f36947ce
Source dataset
uspto-grants-2010_05
Patent number
US07714003B2

Reaction notes

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