Hydrochloric Acid → 2-Tert-butyl-4-bromo-5-nitrophenol

HRID 470037Notes

Reaction equation

HRID 470037 reaction equation
C(=O)([O:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([Br:14])=[CH:7][C:6]=1[C:15]([CH3:18])([CH3:17])[CH3:16])OC.[OH-].[K+].Cl>CO>[C:15]([C:6]1[CH:7]=[C:8]([Br:14])[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]=1[OH:4])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 574702354-Bromo-2-(tert-butyl)-5-nitrophenyl methyl carbonate

Product 1

HCID 574702362-Tert-butyl-4-bromo-5-nitrophenolYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl (2-tert-butyl-4-bromo-5-nitrophenyl) carbonate (121.5 g, 0.366 mol) in methanol (1000 mL) was added potassium hydroxide (30.75 g, 0.549 mol) in portions. After addition, the mixture was stirred at room temperature for 3 h and acidified with 1N HCl to pH 7. Methanol was removed and water was added. The mixture was extracted with ethyl acetate and the organic layer was separated, dried over Na2SO4 and concentrated to give 2-tert-butyl-4-bromo-5-nitro-phenol (C-14-a) (100 g, 99%).

Workup

  1. additionAfter addition
  2. customMethanol was removed
  3. additionwater was added
  4. extractionThe mixture was extracted with ethyl acetate
  5. customthe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7c3623b0bd9040c89e81f3a2b657c63b
Source dataset
uspto-grants-2014_01
Patent number
US08629162B2

Reaction notes

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