Sodium Carbonate → 4'-(Trifluoromethyl)[1,1'-biphenyl]-3-methanol

HRID 1391730Notes

Reaction equation

HRID 1391730 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:9]=[CH:8][CH:7]=[C:4]([CH2:5][OH:6])[CH:3]=2)=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 851413-Bromobenzyl alcoholHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 144680034'-(Trifluoromethyl)[1,1'-biphenyl]-3-methanol

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture 3-bromobenzyl alcohol (500 mg, 2.70 mmol), 4-(triflouromethyl)benzeneboronic acid (1.01 g, 5.35 mmol), Pd(PPh3)4 (68 mg, 0.06 mmol) and Na2CO3 (740 mg, 7.02 mmol) in a mixture of DME (20 mL) and water (10 mL) was heated at reflux for 3 hours. The mixture was allowed to cool to rt, and then partitioned between EtOAc and water. The layers were separated and the aqueous re-extracted with EtOAc (2×) and the combined organic layer washed with water and then brine, dried (Na2SO4), filtered and reduced to give an oil. Purification by flash chromatography (silica) eluting with cyclohexane:EtOAc (5:2) afforded the title compound as a clear oil which crystallised on standing (654 mg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. custompartitioned between EtOAc and water
  4. customThe layers were separated
  5. extractionthe aqueous re-extracted with EtOAc (2×)
  6. washthe combined organic layer washed with water
  7. dry with materialbrine, dried (Na2SO4)
  8. filtrationfiltered
  9. customto give an oil
  10. customPurification by flash chromatography (silica)
  11. washeluting with cyclohexane:EtOAc (5:2)

Sources & evidence

ORD record
ord-d29b84b4c567476b8cacdcdc99677da1
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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