(Dimethyl sulfide)trihydroboron → (1-(4-Bromophenyl)cyclopropyl)methanol

HRID 1474645Notes

Reaction equation

HRID 1474645 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11](O)=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CSC.B>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:11][OH:12])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 162279661-(4-Bromophenyl)cyclopropane-1-carboxylic acid

Product 1

HCID 20252945(1-(4-Bromophenyl)cyclopropyl)methanolYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-bromophenyl)cyclopropane carboxylic acid (3.0 g, 12.4 mmol) in dry THF (40 mL) under nitrogen atmosphere, was added borane dimethyl sulphide (8.83 mL, 19.8 mmol, 2 M solution in DCM) at 0° C. The reaction mixture was stirred at r.t for 4 h. After the completion of reaction as confirmed by TLC, the reaction mixture was quenched by dropwise addition of methanol until effervescence stopped. Volatiles were evaporated in vacuo and the compound was diluted with ethyl acetate (80 mL). The organic layer was separated; washed with water (3×10 mL), dried over Na2SO4 and concentrated. The crude product obtained was purified by column chromatography (silica gel, 1:4 EtOAc:Pet Ether) to afford title compound (2.7 g, 96%) as a solid.

Workup

  1. customAfter the completion of reaction
  2. customthe reaction mixture was quenched by dropwise addition of methanol until effervescence
  3. customVolatiles were evaporated in vacuo
  4. additionthe compound was diluted with ethyl acetate (80 mL)
  5. customThe organic layer was separated
  6. washwashed with water (3×10 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe crude product obtained
  10. customwas purified by column chromatography (silica gel, 1:4 EtOAc:Pet Ether)

Sources & evidence

ORD record
ord-f2f32c492331437fbc13e3b1012847a0
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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