Borane;tetrahydrofuran → 4-Bromo-2-ethylbenzenemethanol

HRID 859670Notes

Reaction equation

HRID 859670 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([CH2:11][CH3:12])[CH:3]=1.B.C1COCC1>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[C:4]([CH2:11][CH3:12])[CH:3]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 106570054-Bromo-2-ethylbenzoic acid

Product 1

HCID 587642724-Bromo-2-ethylbenzenemethanolYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-2-ethyl-benzoic acid (115 mmol) in anhydrous THF (380 mL) at 0° C. was added BH3.THF complex (1.0 N solution in THF, 230 mL) over 30 min. The resulting mixture was slowly warmed up to room temperature and the stirred for 15 hours. The reaction was carefully quenched with slow addition of water. The solvent was removed and the residue was taken up in EtOAc. The organic layer was washed with 1.0 N HCl, H2O, brine and dried over MgSO4. The solvent was removed to afford the desired product. (22 g, 89% yield). 1H NMR (300 MHz, CDCl3): δ 1.23 (t, J=7.5 Hz, 3 H), 2.64–3.01 (m, 2H), 4.68 (s, 2H), 7.24–7.26 (m, 1H), 7.32–7.36 (m, 2H).

Workup

  1. customThe reaction was carefully quenched with slow addition of water
  2. customThe solvent was removed
  3. washThe organic layer was washed with 1.0 N HCl, H2O, brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-ac0519f28dd1474cb495d7270187decf
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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