Water → Benzenamine, 2-bromo-6-fluoro-4-methyl-

HRID 2061493Notes

Reaction equation

HRID 2061493 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[Br:10]N1C(=O)CCC1=O.O>C(O)(=O)C>[Br:10][C:7]1[CH:8]=[C:2]([CH3:1])[CH:3]=[C:4]([F:9])[C:5]=1[NH2:6]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 679842-Fluoro-4-methylaniline

Product 1

HCID 26598247Benzenamine, 2-bromo-6-fluoro-4-methyl-Yield 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of 4-methyl-2-fluoroaniline (15 g, 0.12 mol) in acetic acid (120 ml) at 15° C. under argon was treated portionwise over 20 minutes with solid N-bromosuccinimide (24 g, 0.135 mol), then allowed to warm to room temperature and stirred for 1 hr. The reaction mixture was treated with water (500 ml) and extracted with ethyl acetate (2×300 ml). The combined extract was washed with water (2×500 ml), then excess 10% Na2CO3 solution (400 ml). The ethyl acetate solution was dried (Na2SO4) and concentrated under vacuum to leave the title compound as a dark red oil (24.0 g, 98%).

Workup

  1. extractionextracted with ethyl acetate (2×300 ml)
  2. extractionThe combined extract
  3. washwas washed with water (2×500 ml)
  4. dry with materialThe ethyl acetate solution was dried (Na2SO4)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1937359d1aac4a05990ab9dea44d01d9
Source dataset
uspto-grants-2012_10
Patent number
US08283364B2

Reaction notes

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