Water → (R)-2-(2-bromo-3-methylbutyryl)amino-6-isopropylphenol

HRID 622376Notes

Reaction equation

HRID 622376 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]([CH3:11])[CH3:10])[C:4]=1[OH:12].O.C(=O)(O)[O-].[Na+].[Br:19][C@H:20]([CH:24]([CH3:26])[CH3:25])[C:21](Cl)=[O:22]>C(OCC)(=O)C>[Br:19][C@H:20]([CH:24]([CH3:26])[CH3:25])[C:21]([NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]([CH3:10])[CH3:11])[C:4]=1[OH:12])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 212930372-Amino-6-isopropylphenol hydrochlorideHCID 22839824(R)-2-bromo-3methylbutyryl chloride

Product 1

HCID 6932486(R)-2-(2-bromo-3-methylbutyryl)amino-6-isopropylphenolYield 76.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred, ice-cooled mixture of 2-amino-6-isopropylphenol hydrochloride (15.0 g), ethyl acetate (200 ml), water (100 ml), and sodium bicarbonate (20.0 g), was added dropwise a solution of (R)-2-bromo-3methylbutyryl chloride (16.0 g) in ethyl acetate (30 ml). The whole was stirred for 30 minutes, and the ethyl acetate layer was separated, washed with water and dried over MgSO4. Removal of the solvent gave (R)-2-(2-bromo-3-methylbutyryl)amino-6-isopropylphenol as crystals (19.1 g, 76.1%). Recrystallization from isopropyl ether afforded colorless needles, mp 108°-109° C. [α]D23 +44.8° (c=0.82, MeOH).

Workup

  1. temperatureTo a stirred, ice-cooled
  2. customthe ethyl acetate layer was separated
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-2f24d0c71b41437d93d6c3ff70833fcb
Source dataset
uspto-grants-1988_09
Patent number
US04771050

Reaction notes

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