3-Bromobenzoic acid → 3-Bromobenzyl alcohol

HRID 2372898Notes

Reaction equation

HRID 2372898 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:8]=[CH:9][CH:10]=1

Participants

3

Reactant 1

HCID 114563-Bromobenzoic acid

Product 1

HCID 851413-Bromobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 50.0 g (0.25 mols, Aldrich) of 3-bromobenzoic acid in 100 ml of dry tetrahydrofuran (THF) cooled to 0° is added slowly 100 ml (1.0M in THF, 100 mmols, Aldrich) of borane-tetrahydrofuran complex. The reaction is stirred at 0° for 1 hour then at room temperature for 18 hours. The reaction is quenched by dropwise addition of water then concentrated in vacuo to remove solvent. The residue is partitioned between diethyl ether and 1M aqueous HCl. The organic layer is separated, washed with 1M aqueous sodium hydroxide, brine, dried (magnesium sulfate) and concentrated in vacuo to afford title compound.

Workup

  1. additionis added slowly 100 ml (1.0M in THF, 100 mmols, Aldrich) of borane-tetrahydrofuran complex
  2. waitat room temperature for 18 hours
  3. customThe reaction is quenched by dropwise addition of water
  4. concentrationthen concentrated in vacuo
  5. customto remove solvent
  6. customThe residue is partitioned between diethyl ether and 1M aqueous HCl
  7. customThe organic layer is separated
  8. washwashed with 1M aqueous sodium hydroxide, brine
  9. dry with materialdried (magnesium sulfate)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4bff526cc695448c9707e1261c7f3dfa
Source dataset
uspto-grants-1992_03
Patent number
US05100889

Reaction notes

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