Methanol → (5-Bromo-2-chloro-3-methoxyphenyl)methanol

HRID 576330Notes

Reaction equation

HRID 576330 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].B(F)(F)F.CSC.CO>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([Cl:11])=[C:6]([CH2:7][OH:8])[CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11137191Trifluoroborane-methyl sulfideHCID 710769615-Bromo-2-chloro-3-methoxybenzoic acid

Product 1

HCID 71110767(5-Bromo-2-chloro-3-methoxyphenyl)methanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of acid 56 (10.1 g, 38.0 mmol) in THF (100 mL) was added borontrifluoride-dimethylsulfide (14.4 mL, 152 mmol) dropwise at 0° C. under an atmosphere of nitrogen. The mixture was stirred at room temperature for 18 hours. MeOH was added to the reaction mixture dropwise at 0° C. The mixture was extracted with EtOAc/H2O (150 mL/150 mL), dried over MgSO4, filtered, and concentrated in vacuo to provide the crude alcohol 57 (9.50 g, 100%) as yellow oil.

Workup

  1. extractionThe mixture was extracted with EtOAc/H2O (150 mL/150 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ed0957ba9e074b33a01823b152695684
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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