Benzene → 2-Bromo-6-(1-methylethyl)benzenamine

HRID 1448917Notes

Reaction equation

HRID 1448917 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([CH3:3])[CH3:2].C1C=CC=CC=1.C1C(=O)N([Br:24])C(=O)C1>>[Br:24][C:7]1[CH:8]=[CH:9][CH:10]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[NH2:6]

Participants

4

Reactant 3

HCID 241BenzeneHCID 125612-IsopropylanilineHCID 67184N-bromobutanimide

Product 1

HCID 121865462-Bromo-6-(1-methylethyl)benzenamine

Procedure

To o-isopropylaniline in 4 l. benzene (0.74 mol, 100 g) was added 131.7 g (0.74 mol) NBS all at once. There was an exotherm to 35° C. Material was stirred two hours, then let stand overnight. The volume was reduced by three-quarters, and solid removed by filtration. Benzene was then removed from the filtrate, pentane added with ice, followed by 40 ml acetic anhydride. After ca. 15 minutes, solid was filtered off, pentane solution separated from filtrate, washed with ammonia water. After evaporation of pentane, oil was distilled 83° C. (0.25 mm) to give 64.5 g of 2-bromo-6-isopropylaniline.

Workup

  1. customto 35° C
  2. waitlet stand overnight
  3. customremoved by filtration
  4. customBenzene was then removed from the filtrate, pentane
  5. additionadded with ice
  6. waitAfter ca. 15 minutes
  7. filtrationsolid was filtered off
  8. custompentane solution separated from filtrate
  9. washwashed with ammonia water
  10. customAfter evaporation of pentane, oil
  11. distillationwas distilled 83° C. (0.25 mm)

Sources & evidence

ORD record
ord-b5cfe57d415c417ba301334ebd86772a
Source dataset
uspto-grants-1980_02
Patent number
US04188342

Reaction notes

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