Water → 2-(3,5-Bis-trifluoromethyl-benzyloxymethyl)-biphenyl

HRID 1267512Notes

Reaction equation

HRID 1267512 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH2:13][OH:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O.C(Cl)Cl>CN(C)C=O.[Cl-].[Na+].O>[F:1][C:2]([F:15])([F:16])[C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1)[CH2:13][O:14][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 1229333,5-Bis(trifluoromethyl)benzyl alcoholHCID 219728202-(Chloromethyl)-1,1'-biphenyl

Product 1

HCID 185465002-(3,5-Bis-trifluoromethyl-benzyloxymethyl)-biphenylYield 48.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 1.53 g (6.26 mmol)(3,5-bis-trifluoromethyl-phenyl)-methanol in 15 ml N,N-dimethylformamide 0.30 g (7.52 mmol) sodiumhydride (60% dispersion in mineral oil) was added and the reaction mixture was stirred for 1 hr. After the addition of 1.27 g (6.26 mmol) 2-chloromethyl-biphenyl in 5 ml N,N-dimethylformamide at 0°, the reaction mixture was stirred for 3 hrs. at RT. The reaction mixture was distributed between 50 ml H2O, 50 ml brine and 50 ml CH2Cl2. The phases were separated, the aqueous layer washed twice with 50 ml CH2Cl2. The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, hexane/ethyl acetate 40:1) to give 1.25 g (47%) 2-(3,5-bis-trifluoromethyl-benzyloxymethyl)-biphenyl as a colorless oil, MS (EI): 410 (M+).

Workup

  1. stirringthe reaction mixture was stirred for 3 hrs
  2. customat RT
  3. customThe phases were separated
  4. washthe aqueous layer washed twice with 50 ml CH2Cl2
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography (SiO2, hexane/ethyl acetate 40:1)

Sources & evidence

ORD record
ord-9989a3a214814205af9cba7f92f079fb
Source dataset
uspto-grants-2003_04
Patent number
US06552088B2

Reaction notes

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