Bromine → N-(4-Bromo-3-fluoro-2-methylphenyl)acetamide

HRID 751146Notes

Reaction equation

HRID 751146 reaction equation
[F:1][C:2]1[C:3]([CH3:12])=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[Br:13]Br>C(O)(=O)C>[Br:13][C:7]1[CH:6]=[CH:5][C:4]([NH:8][C:9](=[O:11])[CH3:10])=[C:3]([CH3:12])[C:2]=1[F:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 1489284N-(3-fluoro-2-methylphenyl)acetamide

Product 1

HCID 67123438N-(4-Bromo-3-fluoro-2-methylphenyl)acetamideYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of N-(3-fluoro-2-methylphenyl)acetamide (72A) (1.71 g, 10.2 mmol) in acetic acid (15 mL) at 0° C. was added bromine (1.68 mL, 32.8 mmol) over 15 min. The mixture was stirred at rt for 2 h, and was then poured into ice (50 g). The mixture was filtered and concentrated under reduced pressure to give the title compound (2.26 g). LCMS: m/z 246 [M+H]+

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-278caa0afd7d401991e0b73df53d0909
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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