2-Bromo-5-nitrobenzoic acid → (2-Bromo-5-nitrophenyl)methanol

HRID 1057508Notes

Reaction equation

HRID 1057508 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4](O)=[O:5].B.C1COCC1>O1CCCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 2430252-Bromo-5-nitrobenzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 18671373(2-Bromo-5-nitrophenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a stirring solution of 2-bromo-5-nitrobenzoic acid (1 eq) in tetrahydrofuran (0.4 M) at 0° C. under nitrogen was added BH3/THF (1 M) (1.5 eq). The reaction mixture was stirred at 70° C. for 1 hr and quenched with methanol. The reaction mixture was concentrated in vacuo to afford the product. EI-MS m/z 232 (M+H)+.

Workup

  1. customquenched with methanol
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto afford the product

Sources & evidence

ORD record
ord-098594bda92d4387b2300d3a238bbc1a
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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