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

HRID 1471346Notes

Reaction equation

HRID 1471346 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Br:5][C:6]1[CH:7]=[C:8]([O:12][CH3:13])[CH:9]=[CH:10][CH:11]=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl.O.Cl>[Br:5][C:6]1[CH:7]=[C:8]([O:12][CH3:13])[CH:9]=[CH:10][C:11]=1[C:1](=[O:3])[CH3:2]

Participants

7

Reactant 3

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

Product 1

HCID 106570061-(2-Bromo-4-methoxyphenyl)ethan-1-oneYield 83.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Acetyl chloride (3.56 mL, 0.06 mol) is added dropwise to a stirred suspension of 3-bromoanisole (9.35 g, 0.05 mol) and AlCl3 (8.00 g, 0.06 mol) in dichloromethane (50 mL) at 0° C. under argon. The resulting mixture is stirred at 0° C. for 40 min and then at room temperature for 1 h, and diluted with H2O (100 mL) and 2 N HCl (35 mL), and extracted with ethyl acetate (2×100 mL and 50 mL). The extract is washed (brine) and dried. After solvent removal at reduced pressure, the residue is purified on silica gel (12.5% to 14.3% ethyl acetate/hexane) to give 9.55 g (83%) of 2 as a colorless liquid. IR 2964, 1688, 1596, 1252 cm−1; 1H NMR (CDCl3) δ 2.66 (s, 3H, CH3CO), 3.88 (s, 3H, CH3O), 6.91 (dd, J=8.4 Hz, 2.4 Hz, 1H, 5-PhH), 7.19 (d, J=2.4 Hz, 1H, 3-PhH), 7.63 ppm (d, J=8.4 Hz, 1H, 6-PhH).

Workup

  1. waitat room temperature for 1 h
  2. extractionextracted with ethyl acetate (2×100 mL and 50 mL)
  3. washThe extract is washed (brine)
  4. customdried
  5. customAfter solvent removal at reduced pressure
  6. customthe residue is purified on silica gel (12.5% to 14.3% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0ee9a385bf294efeaaa86f40aa982dc3
Source dataset
uspto-grants-2015_04
Patent number
US09012217B2

Reaction notes

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