Methanol → (3-(Bromomethyl)phenyl)methanol

HRID 1049528Notes

Reaction equation

HRID 1049528 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6](OC)=[O:7].[H-].C([Al+]CC(C)C)C(C)C.CO>C1(C)C=CC=CC=1>[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:6][OH:7])[CH:10]=[CH:11][CH:12]=1

Participants

5

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, to a solution of methyl 3-(bromomethyl)benzoate (10.0 g) in toluene (100 mL) was added a 1.5 M solution (100 mL) of diisobutylaluminum hydride in toluene at 0° C., and the mixture was stirred at 0° C. for 1 hr. To the reaction mixture was added methanol at 0° C., and the resulting white precipitate was filtered off. The solvent in the filtrate was evaporated under reduced pressure to give a crude product of the title compound (8.83 g) as a colorless oil. This compound was used for the next step without further purification.

Workup

  1. filtrationthe resulting white precipitate was filtered off
  2. customThe solvent in the filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1c91de5961e448309a01d640baa274dd
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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