Borane → (2-Bromo-5-methoxyphenyl)methanol

HRID 2393577Notes

Reaction equation

HRID 2393577 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4](O)=[O:5].B>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 6331BoraneHCID 899062-Bromo-5-methoxybenzoic acid

Product 1

HCID 10867706(2-Bromo-5-methoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-bromo-5-methoxybenzoic acid (10.00 g, 43.3 mmol) in dry THF (40 ml) was treated with borane in THF (65 ml of 1.0M solution, 65 mmol) at room temperature under nitrogen. After stirring for 4 h, no starting material was detectable by tic. Excess borane was quenched by careful addition of water over 30 min, and the solvent was evaporated under reduced pressure. The residue was partitioned between ether and 5% Na2CO3. The ether layer was washed with 5% Na2CO3, water, and brine, and dried over MgSO4. Filtration and removal of solvent left a colorless oil which solidified (9.11 g, 97%); tlc (silica gel, CH2Cl2, Rf 0.25). This material was used without further purification.

Workup

  1. customExcess borane was quenched by careful addition of water over 30 min
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was partitioned between ether and 5% Na2CO3
  4. washThe ether layer was washed with 5% Na2CO3, water, and brine
  5. dry with materialdried over MgSO4
  6. filtrationFiltration and removal of solvent
  7. waitleft a colorless oil which
  8. customThis material was used without further purification

Sources & evidence

ORD record
ord-d01c5ab4dea445a8ac97cc882bcf8a38
Source dataset
uspto-grants-1998_09
Patent number
US05807897

Reaction notes

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