Sodium Carbonate → N,O-di-(3,5-di-t-butyl-4-hydroxy-phenylacetyl)-6-amino-2-bromo-4-chloro-phenol

HRID 840188Notes

Reaction equation

HRID 840188 reaction equation
[C:1](=[O:4])([O-])[O-:2].[Na+].[Na+].[NH2:7][C:8]1[C:13](O)=[C:12]([Br:15])[CH:11]=[C:10]([Cl:16])[CH:9]=1.[C:17]([C:21]1[CH:22]=[C:23]([CH2:32][C:33](Cl)=[O:34])[CH:24]=[C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:26]=1[OH:27])([CH3:20])([CH3:19])[CH3:18].S(Cl)(Cl)=O>O>[C:17]([C:21]1[CH:22]=[C:23]([CH2:32][C:33]([NH:7][C:8]2[C:13]([O:2][C:1](=[O:4])[CH2:32][C:23]3[CH:22]=[C:21]([C:17]([CH3:18])([CH3:20])[CH3:19])[C:26]([OH:27])=[C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:24]=3)=[C:12]([Br:15])[CH:11]=[C:10]([Cl:16])[CH:9]=2)=[O:34])[CH:24]=[C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:26]=1[OH:27])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 107316503,5-Di-t-butyl-4-hydroxy-phenylacetyl chlorideHCID 155210892-Amino-6-bromo-4-chlorophenol

Product 1

HCID 15521188N,O-di-(3,5-di-t-butyl-4-hydroxy-phenylacetyl)-6-amino-2-bromo-4-chloro-phenolYield 103.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Water (173 ml) and sodium carbonate (33.24 g, 310 mmol) were added to a stirred ethereal solution (123 ml) of 6-amino-2-bromo-4-chloro-phenol (17.45 g, 78.4 mmol). After 15 minutes 3,5-di-t-butyl-4-hydroxy-phenyl acetyl chloride (47.60 g, 93.1%, 156.8 mmol) (prepared with thionyl chloride from the corresponding acid), was added at −5E to 0EC and stirring continued for a further 1.5 hours without cooling. The aqueous phase was adjusted to pH 8 and the layers separated. The organics were washed with 1 N HCl (100 ml) and saturated aqueous sodium bicarbonate solution (100 ml), dried (Na2SO4) and evaporated into give 58.1 g (103.6%) of the title compound which was suitable for the next step.

Workup

  1. additionwas added at −5E to 0EC
  2. temperaturewithout cooling
  3. customthe layers separated
  4. washThe organics were washed with 1 N HCl (100 ml) and saturated aqueous sodium bicarbonate solution (100 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-9b5737df890d40108533544f0472ed5a
Source dataset
uspto-grants-2002_04
Patent number
US06365606B1

Reaction notes

Loading…