Water → 2-(2-Bromo-3-methylbutyryl)aminophenol

HRID 622372Notes

Reaction equation

HRID 622372 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])O.[Na+].O.[Br:15][CH:16]([CH:20]([CH3:22])[CH3:21])[C:17](Cl)=[O:18]>C(OCC)(=O)C>[Br:15][CH:16]([CH:20]([CH3:22])[CH3:21])[C:17]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 58012-AminophenolHCID 516892Sodium BicarbonateHCID 124869822-Bromo-3-methylbutanoyl chloride

Product 1

HCID 142346662-(2-Bromo-3-methylbutyryl)aminophenol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 2-aminophenol (27 25 g), sodium hydrogencarbonate (31.5 g), ethyl acetate (250 ml), and water (200 ml), a solution of 2-bromo-3-methylbutyryl chloride (49.8 g) in ethyl acetate (100 ml) was added dropwise with ice-cooling and with stirring. After stirring with ice-cooling for further 1 hour, the ethyl acetate layer was separated, washed with water, and dried (MgSO4), and the solvent was evaporated off. The residue was crystallized from hexane, to give 2-(2-bromo-3-methylbutyryl)aminophenol. Yield was 59.7 g (87.9%). Recrystallization from isopropyl ether gave colorless prisms, mp 110°-111° C.

Workup

  1. temperaturecooling
  2. stirringAfter stirring with ice-
  3. temperaturecooling for further 1 hour
  4. customthe ethyl acetate layer was separated
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. customthe solvent was evaporated off
  8. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-3cdf2d7774da4f11af7102dc3fd8608c
Source dataset
uspto-grants-1988_09
Patent number
US04771050

Reaction notes

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