Lithium triethylborohydride → (3-Bromo-2-chlorophenyl)methanol

HRID 1465776Notes

Reaction equation

HRID 1465776 reaction equation
[Br:1][C:2]1[C:3]([Cl:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](OC)=[O:6].[Li+].[B-](CC)(CC)CC>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[C:3]([Cl:12])=[C:4]([CH2:5][OH:6])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 23712863Lithium triethylborohydrideHCID 67516858Methyl 3-bromo-2-chlorobenzoate

Product 1

HCID 67146654(3-Bromo-2-chlorophenyl)methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-bromo-2-chlorobenzoate (1.9 g, 7.6 mmol) in THF (30 mL) was added Super Hydride (23 mL, 23 mmol) at 0° C. The reaction was allowed to stir for 16 hours. The reaction was diluted with EtOAc, washed with brine, dried over sodium sulfate, and purified by MPLC to provide (3-bromo-2-chlorophenyl)methanol. LC-MS (IE, m/z): 205 [M−17]+;

Workup

  1. washwashed with brine
  2. dry with materialdried over sodium sulfate
  3. custompurified by MPLC

Sources & evidence

ORD record
ord-efa4b3f766694e9b98ad645a2fa9227e
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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