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

HRID 2173189Notes

Reaction equation

HRID 2173189 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. TLC showed clean reaction. The reaction was diluted with EtOAc, washed with brine, dried over sodium sulfate, and purified by MPLC to furnish (3-bromo-2-chlorophenyl)methariol. LC-MS (IE, m/z): 205 [M-17]+;

Workup

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

Sources & evidence

ORD record
ord-70e472bf31484c2aa72e804ef4cf7dd7
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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