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

HRID 1840870Notes

Reaction equation

HRID 1840870 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>C(Cl)Cl>[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-Bromoaniline2×HCID 8471TriethylamineHCID 1023943-Methyl-2-butenoyl chloride2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,3-Dimethylacryloyl chloride (Intermediate 1, 4.16 g, 35.1 mmol) was slowly added to a solution of 4-bromoaniline (Intermediate 2, 5.00 g, 29.2 mmol) in 25 mL of methylene chloride. 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 then poured on 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 as a yellow solid (7.43 g, 100% yield).

Workup

  1. stirringThe resulting solution was stirred at room temperature for 3 h
  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-aeb5676b33124a8ba1cae4b09884f352
Source dataset
uspto-grants-2004_01
Patent number
US06683092B1

Reaction notes

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