Hydrochloric Acid → 2-Bromo-4-chloro-6-(3,5-di-t-butyl-4-hydroxy-phenylacetyl-amino)-phenol

HRID 842088Notes

Reaction equation

HRID 842088 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][C:17]([NH:19][C:20]2[C:25]([O:26]C(=O)CC3C=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=3)=[C:24]([Br:45])[CH:23]=[C:22]([Cl:46])[CH:21]=2)=[O:18])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl>CO>[Br:45][C:24]1[CH:23]=[C:22]([Cl:46])[CH:21]=[C:20]([NH:19][C:17](=[O:18])[CH2:16][C:7]2[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]([OH:11])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=2)[C:25]=1[OH:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 15521188N,O-di-(3,5-di-t-butyl-4-hydroxy-phenylacetyl)-6-amino-2-bromo-4-chloro-phenol

Product 1

HCID 155211892-Bromo-4-chloro-6-(3,5-di-t-butyl-4-hydroxy-phenylacetyl-amino)-phenolYield 88.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N,O-Di-(3,5-di-t-butyl-4-hydroxy-phenylacetyl)-6-amino-2-bromo-4-chloro-phenol (58.1 g, 89.8 mmol) in methanol (400 ml) and potassium carbonate (24.78 g, 180 mmol) was stirred at room temperature for 10 minutes. The methanol was removed in-vacuo, the residue treated with 2 N HCl (180 ml, 360 mmol), and extracted with ethyl acetate (300 ml). The organics were dried (Na2SO4), evaporated in-vacuo, and the residue suspended in petroleum ether. The precipitate was collected to give 37.44 g (88.9%) of the title compound which was suitable for the next step.

Workup

  1. customThe methanol was removed in-vacuo
  2. extractionextracted with ethyl acetate (300 ml)
  3. dry with materialThe organics were dried (Na2SO4)
  4. customevaporated in-vacuo
  5. customThe precipitate was collected

Sources & evidence

ORD record
ord-07ca5195ccca4d1c85b584b3d1525b75
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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