Hexane → 2-Bromo-1-(4-bromo-2-fluorophenyl)ethanone

HRID 1436412Notes

Reaction equation

HRID 1436412 reaction equation
[Br:1]Br.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[C:6]([F:13])[CH:5]=1.C(OCC)(=O)C.CCCCCC>C(O)(=O)C.C(Cl)Cl>[Br:1][CH2:11][C:10]([C:7]1[CH:8]=[CH:9][C:4]([Br:3])=[CH:5][C:6]=1[F:13])=[O:12]

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 24408BromineHCID 219385811-(4-Bromo-2-fluorophenyl)ethan-1-one

Product 1

HCID 221214832-Bromo-1-(4-bromo-2-fluorophenyl)ethanoneYield 97%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Bromine (1.2 mL, 23.0 mmol) in 10 mL of glacial acetic acid was added drop-wise to a solution of 1-(4-bromo-2-fluoro-phenyl)-ethanone (5.0 g, 23.0 mmol), prepared in the previous step, in 150 mL of dry methylene chloride at 0° C. After the addition, the reaction was allowed to warm to room temperature. TLC (5% ethyl acetate:hexane) indicated the starting material was consumed. The reaction was diluted with methylene chloride and washed with 5% sodium thiosulfate and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 2-bromo-1-(4-bromo-2-fluoro-phenyl)-ethanone (6.6 g, 97%) as a light green oil. This compound was used without further purification. MS (ES) m/z 297 [M+H]+.

Workup

  1. additionAfter the addition
  2. customwas consumed
  3. additionThe reaction was diluted with methylene chloride
  4. washwashed with 5% sodium thiosulfate and brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f19e8f0b3ac4465a9ce0100b1bdd1b5b
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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