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

HRID 1377537
Notes
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Reaction equation

HRID 1377537 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 mM) were added to a stirred ethereal solution (123 ml) of 6-amino-2-bromo-4-chloro-phenol (17.45 g, 78.4 mM). After 15 minutes 3,5-di-t-butyl-4-hydroxy-phenylacetyl chloride (47.60 g, 93.1%, 156.8 mM) (prepared with thionyl chloride from the corresponding acid), was added at -5° to 0° C. 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 1N HCl (100 ml) and saturated aqueous sodium bicarbonate solution (100 ml), dried (Na2SO4) and evaporated in-vacuo to give 58.1 g (103.6%) of the title compound which was suitable for the next step.

Workup

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

Sources & evidence

ORD record
ord-38fede7e3c3e478bb583dbd2b2a59cfe
Source dataset
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05665737

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes