Bromine → N-[4-(2-BROMOACETYL)-3-FLUOROPHENYL]acetamide

HRID 507407Notes

Reaction equation

HRID 507407 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[CH:6][C:5]=1[F:14])(=[O:3])[CH3:2].[Br:15]Br>C(Cl)(Cl)Cl>[Br:15][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[CH:6][C:5]=1[F:14])=[O:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 14621109N-(4-Acetyl-3-fluorophenyl)acetamide

Product 1

HCID 86346474N-[4-(2-BROMOACETYL)-3-FLUOROPHENYL]acetamideYield 82.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-(4-Acetyl-3-fluoro-phenyl)-acetamide (10.2 g, 51.2 mmol) is dissolved in 50 mL chloroform. At room temperature bromine (1.98 mL, 38.4 mmol) is added drop wise. The reaction mixture is stirred at room temperature for 1.5 hours. Subsequently the precipitated product is filtered off, washed first with chloroform and then with ethyl acetate to yield N-[4-(2-bromo-acetyl)-3-fluoro-phenyl]-acetamide (8.7 g, 43%); LCIMS at 254 nm; [M+H] 275; Rt 2.918 min)

Workup

  1. filtrationSubsequently the precipitated product is filtered off
  2. washwashed first with chloroform

Sources & evidence

ORD record
ord-36ad943755504f6d9a194d0e76d4286b
Source dataset
uspto-grants-2010_08
Patent number
US07786155B2

Reaction notes

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