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

HRID 392874Notes

Reaction equation

HRID 392874 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)methanolYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 25 g (0.11 mol) of 2-bromo-5-methoxybenzoic acid was dissolved in 100 mL of anhydrous THF. 140 mL (0.14 mol) of borane (1 M in THF) was added to this solution over a period of 1 hour. The reaction was allowed to stir and was carefully quenched with 1:1 THF: saturated K2CO3. Ether was added and the aqueous and organic layers were separated. The aqueous layer was extrated again with ether (2×100 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to afford 23.0 g (96%) of 2-bromo-5-methoxybenzyl alcohol (13).

Workup

  1. customwas carefully quenched with 1:1 THF
  2. additionEther was added
  3. customthe aqueous and organic layers were separated
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be673014c4754bdc8913a89175752716
Source dataset
uspto-grants-2004_10
Patent number
US06803470B2

Reaction notes

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