4-Bromoaniline → 2-Butenamide, N-(4-bromophenyl)-3-methyl-

HRID 1453629Notes

Reaction equation

HRID 1453629 reaction equation
[CH3:1][C:2]([CH3:7])=[CH:3][C:4](Cl)=[O:5].[Br:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1.C(N(CC)CC)C>ClCCl>[Br:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][C:4](=[O:5])[CH:3]=[C:2]([CH3:7])[CH3:1])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 8471TriethylamineHCID 1023943-Methyl-2-butenoyl chloride

Product 1

HCID 5320952-Butenamide, N-(4-bromophenyl)-3-methyl-Yield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,3-Dimethylacryloyl chloride (available from Aldrich, 4.16 g, 35.1 mmol) was slowly added to a solution of 4-bromoaniline (5.00 g, 29.2 mmol) in 25 mL of dichloromethane. After stirring at room temperature for 20 min triethylamine (2.5 mL) was added dropwise to the mixture. The resulting solution was stirred at room temperature for 3 h and poured to 100 mL of ice-water mixture. The organic layer was separated, washed with brine (2×20 mL), dried (MgSO4) and concentrated at reduced pressure to give a yellow residue. Purification by flash chromatography (90:10 hexane/ethyl acetate) afforded the title compound (7.43 g, 100% yield) as a yellow solid: 1H NMR (CDCl3, 300 MHz) δ 7.34 (s, 4H), 7.1 (bs, 1H), 5.69 (s, 1H), 2.23 (s, 3H), 1.91 (s, 3H).

Workup

  1. additionwas added dropwise to the mixture
  2. customThe organic layer was separated
  3. washwashed with brine (2×20 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated at reduced pressure
  6. customto give a yellow residue
  7. customPurification by flash chromatography (90:10 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0fc6279afb7b4d49b905997e57fb3519
Source dataset
uspto-grants-2009_01
Patent number
US07476673B2

Reaction notes

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