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

HRID 916865Notes

Reaction equation

HRID 916865 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.C(=O)(O)[O-].[Na+]>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

5

Reactant 3

HCID 6331BoraneHCID 899062-Bromo-5-methoxybenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 10867706(2-Bromo-5-methoxyphenyl)methanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolve 2-bromo-5-methoxy-benzoic acid (2.25 g, 9.7 mmol) in THF (10 mL) and cool to 0° C. Add 1M borane in THF (48 mL, 48 mmol) and warm to room temperature. Upon completion, slowly pour reaction onto ice and saturated aqueous sodium bicarbonate. Extract with ethyl acetate and wash organic layer with water and saturated aqueous sodium bicarbonate. Dry with sodium sulfate, filter and concentrate in vacuo to yield 2.1 g (100%) of the title compound. 1H NMR (CDCl3) δ7.42 (d, J=8.8 Hz, 1H), 7.06 (d, J=3.1 Hz, 1H), 6.72 (dd, J=8.8, 3.1 Hz, 1H), 4.71 (s, 2H), 3.81 (s, 3H).

Workup

  1. temperaturewarm to room temperature
  2. extractionExtract with ethyl acetate
  3. washwash organic layer with water and saturated aqueous sodium bicarbonate
  4. dry with materialDry with sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-47f28325ae564391a6b75593cbad2435
Source dataset
uspto-grants-2007_09
Patent number
US07271264B2

Reaction notes

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