(Dimethyl sulfide)trihydroboron → Methyl-4,5-dichloro-2-(hydroxymethyl)benzoate

HRID 1681944Notes

Reaction equation

HRID 1681944 reaction equation
[C:1]([C:5]1[CH:13]=[C:12]([Cl:14])[C:11]([Cl:15])=[CH:10][C:6]=1[C:7](O)=[O:8])([O:3][CH3:4])=[O:2].B.CSC>C1COCC1>[CH3:4][O:3][C:1](=[O:2])[C:5]1[CH:13]=[C:12]([Cl:14])[C:11]([Cl:15])=[CH:10][C:6]=1[CH2:7][OH:8]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 198042632-Carbomethoxy 4,5-dichlorobenzoic acid

Product 1

HCID 19804259Methyl-4,5-dichloro-2-(hydroxymethyl)benzoateYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step A (1.06 g, 4.28 mmol) in 5 mL of THF at 0° C. was added borane-methyl sulfide (6.42 mL of 2M solution in THF, 12.84 mmol, 3.0 eq). The reaction was allowed to warm to room temperature. After 16 hours the reaction was cooled to 0° C. and quenched with methanol. The volatiles were removed in vacuo and the oil flash chromatographed with 2:1 hexane/ethyl acetate to yield the titled compound (169 mg, 17%). Approximately 80% of the starting material was also recovered.

Workup

  1. temperatureAfter 16 hours the reaction was cooled to 0° C.
  2. customquenched with methanol
  3. customThe volatiles were removed in vacuo
  4. customthe oil flash chromatographed with 2:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-e7e5948a6b7e41c4a0abe79c11fc1057
Source dataset
uspto-grants-1992_12
Patent number
US05175164

Reaction notes

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