4-Bromo-3-methylaniline → 2-Bromo-N-(4-bromo-3-methylphenyl)acetamide

HRID 490161Notes

Reaction equation

HRID 490161 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].[Br:10][CH2:11][C:12](Cl)=[O:13]>[OH-].[Na+].ClCCl>[Br:10][CH2:11][C:12]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[C:3]([CH3:9])[CH:4]=1)=[O:13]

Participants

5

Reactant 2

HCID 233594-Bromo-3-methylanilineHCID 89602Bromoacetyl chloride

Product 1

HCID 34164002-Bromo-N-(4-bromo-3-methylphenyl)acetamideYield 71%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-Bromo-3-methylaniline (10.08 g, 54.18 mmol) in 2N sodium hydroxide (200 mL) was treated with bromoacetyl chloride (5.00 mL, 60.8 mmol) as a solution in dichloromethane (200 mL) dropwise. After 15 minutes, the layers were separated. The organic phase was washed with 1N hydrochloric acid, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure to provide 11.75 g (71%) of the title compound as a tan solid. 1H NMR (300 MHz, CDCl3) δ 2.39 (s, 3H), 4.01 (s, 2H), 7.23 (m, 1H), 7.44 (d, 1H, J=2.4 Hz), 7.49 (d, 1H, J=8.8 Hz), 8.07 (br s, 1H); MS (DCI/NH3) m/e 306 (M+H)+.

Workup

  1. customthe layers were separated
  2. washThe organic phase was washed with 1N hydrochloric acid
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-45205dd5906f42708ae7ebedd1da114c
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Reaction notes

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