Acetyl chloride → 1-(2-Bromo-4-methoxyphenyl)ethan-1-one

HRID 331386Notes

Reaction equation

HRID 331386 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Al+3].[Cl-].[Cl-].[Cl-].[Br:9][C:10]1[CH:11]=[C:12]([O:16][CH3:17])[CH:13]=[CH:14][CH:15]=1>C(=S)=S>[Br:9][C:10]1[CH:11]=[C:12]([O:16][CH3:17])[CH:13]=[CH:14][C:15]=1[C:1](=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 169713-BromoanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 106570061-(2-Bromo-4-methoxyphenyl)ethan-1-oneYield 51.9%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

A round-bottomed flask was charged acetyl chloride (4.20 g, 53.56 mmol, 1 eq), AlCl3 (7.13 g, 53.56 mmol, 1 eq), and carbon disulfide (80 mL). To the mixture was added dropwise a solution of 3-bromoanisole (9.75 g, 52.13 mmol) in carbon disulfide (20 mL) and stirred for 16 h. The resulting solution was diluted with ice water (100 mL) and extracted with CH2Cl2 (50 mL×3). The extracts were washed with H2O, brine, and 1N NaOH (30 mL). The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexanes=1:10) to afford the title compound (6.2 g, 51%).

Workup

  1. extractionextracted with CH2Cl2 (50 mL×3)
  2. washThe extracts were washed with H2O, brine, and 1N NaOH (30 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (EtOAc/hexanes=1:10)

Sources & evidence

ORD record
ord-7c3ff9b6ba244e32b8c0a66c07591dc1
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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