Benzyl Chloride → 3-(Benzyloxy)-4-bromoaniline

HRID 1006172Notes

Reaction equation

HRID 1006172 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Br:9])=[C:6]([OH:8])[CH:7]=1.CC(C)([O-])C.[K+].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Na]>CN(C)C=O>[CH2:16]([O:8][C:6]1[CH:7]=[C:2]([NH2:1])[CH:3]=[CH:4][C:5]=1[Br:9])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 5360545SodiumHCID 101302845-Amino-2-bromophenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 146595013-(Benzyloxy)-4-bromoanilineYield 106.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-amino-2-bromo-phenol (35.2 g, 0.187 mol) in N,N-dimethylformamide (350 mL) was added potassium tert-butoxide (22.9 g, 0.204 mol). After 15 min, benzyl chloride (25.5 mL, 0.222 mol) was added within 2 min. The reaction was stirred during 4 h and then poured onto an aqueous solution of sodium hydrogenocarbonate and extracted with ethyl acetate. The combined organic phases were washed with brine and water then dried over sodium sulfate, filtered, and evaporated under vacuum. 55.6 g of the title compound were obtained. Black solid, ISP-MS: m/e=279.1 ([M+H]+).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases were washed with brine and water
  3. dry with materialthen dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-b43eee8f84404441b4c8b289a8dc71d9
Source dataset
uspto-grants-2004_09
Patent number
US06787558B2

Reaction notes

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