Acetyl chloride → 1-(3-Bromo-2-fluorophenyl)ethan-1-one

HRID 2358130Notes

Reaction equation

HRID 2358130 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[C:5](Cl)(=[O:7])[CH3:6].C[Si](C)(C)[C:11]1[C:12]([F:18])=[C:13]([Br:17])[CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[Br:17][C:13]1[C:12]([F:18])=[C:11]([C:5](=[O:7])[CH3:6])[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 10340Sodium CarbonateHCID 6451240Aluminum(III) ChlorideHCID 14937357(3-Bromo-2-fluorophenyl)(trimethyl)silane

Product 1

HCID 149373591-(3-Bromo-2-fluorophenyl)ethan-1-oneYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Aluminium trichloride (1.51 g, 11.3 mmol) in dry methylene chloride (10 ml) was cooled to 0° C. and acetyl chloride (0.80 ml, 11.3 mmol) was added in one portion. The mixture was stirred for 15 min. after which a solution of 3-trimethylsilyl-2-fluorobromobenzene (2.33 g, 9.4 mmol) in dry methylene chloride (10 ml) was added dropwise. The mixture was warmed to ambient temperature and stirred for 2 h. The mixture was kept at ambient temperature in a water bath and aqueous sodium carbonate (10%, 50 ml) was added slowly. The aqueous phase was extracted with ethyl acetate (2×50 ml) and the combined organic phase was dried MgSO4), filtered and evaporated. Purification by flash chromatography (ethyl acetate/isooctane, 1:1) yielded the title compound (1.7 g). MS m/z (rel. intensity, 70 eV) 218 (M+, 32), 216 (M+, 34), 203 (bp), 201 (97), 94 (61).

Workup

  1. additionwas added dropwise
  2. customThe mixture was kept at ambient temperature in a water bath
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×50 ml)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography (ethyl acetate/isooctane, 1:1)

Sources & evidence

ORD record
ord-80bae08f20e4491d82f774856ae87b9e
Source dataset
uspto-grants-2010_07
Patent number
US07763639B2

Reaction notes

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