2-Amino-5-bromobenzoic acid → 2-Amino-5-bromobenzenemethanol

HRID 524032

Reaction equation

HRID 524032 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4](O)=[O:5].B.C1COCC1>C1COCC1>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 798582-Amino-5-bromobenzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 110308742-Amino-5-bromobenzenemethanolYield 106.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-5-bromobenzoic acid (10.0 g, 46.3 mmol) in THF (150 mL) was added BH3-THF (1 M, 231 mL) at room temperature, and the reaction mixture was stirred overnight. An aliquot of the reaction mixture was analyzed by LCMS and indicated that the reaction had proceeded to completion. The reaction was quenched with water (150 mL) and extracted with EtOAc (3×500 mL). The organic layers were separated, combined, washed with water (200 mL) and brine (200 mL), dried over sodium sulfate, filtered, and concentrated to afford the title compound (10 g, crude), which was directly used in the next step without further purification. MS (ES+) C7H8BrNO requires: 201. found: 202, 204 [M+H]+.

Workup

  1. customThe reaction was quenched with water (150 mL)
  2. extractionextracted with EtOAc (3×500 mL)
  3. customThe organic layers were separated
  4. washwashed with water (200 mL) and brine (200 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5b3952c678a14f01ad3ab86da6a6cc0c
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Linked notes

Loading…