Water → HCID 11594218, compound

HRID 70732Notes

Reaction equation

HRID 70732 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[O:20]C.[Br-].[Br-].[Br-].B.O>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([C:8]2([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[CH:5]=[CH:4][C:3]=1[OH:20]

Participants

5

Reactant 3

HCID 962WaterHCID 669678242-Fluoro-1-methoxy-4-(1-phenyl-cyclohexyl)-benzeneHCID 178419136HCID 178419136, compound

Product 1

HCID 11594218HCID 11594218, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the crude 2-fluoro-1-methoxy-4-(1-phenyl-cyclohexyl)-benzene in dichloromethane (100 mg, 0.25 mmol, 2 mL) was added to a solution of borane tribromide in dichloromethane (1 M, 0.25 ml, 025 mmol) at −78° C. under an argon atmosphere and stirred at r.t for 3 h. Water (10 mL) was added and the mixture was extracted with dichloromethane (2×10 mL). The combined organic phase was dried (Na2SO4) and concentrated to a syrup. Work-up by flash-chromatography (eluent: 30→80% dichloromethane in heptane) gave the title product in a yield of 50 mg.

Workup

  1. extractionthe mixture was extracted with dichloromethane (2×10 mL)
  2. dry with materialThe combined organic phase was dried (Na2SO4)
  3. concentrationconcentrated to a syrup

Sources & evidence

ORD record
ord-866bb73cb1df47d896ce3a6b8667ab9a
Source dataset
uspto-grants-2014_09
Patent number
US08822548B2

Reaction notes

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