3,5-Bis(trifluoromethyl)benzenesulphonyl chloride → Benzhydrol

HRID 1077990Notes

Reaction equation

HRID 1077990 reaction equation
[CH:1]([OH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NC1C=C(C(F)(F)F)C=CC=1OC1C=CC=CC=1C([O-])=O.FC(F)(F)C1C=C(S(Cl)(=O)=O)C=C(C(F)(F)F)C=1>N1C=CC=CC=1>[CH:1]([OH:14])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5209453,5-Bis(trifluoromethyl)benzenesulphonyl chlorideHCID 131719119Benzhydrol 2-(2-amino-4-trifluoromethylphenoxy)benzoate

Product 1

HCID 7037Benzhydrol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzhydrol 2-(2-amino-4-trifluoromethylphenoxy)benzoate (4 g, 8.6 mmol) was dissolved in pyridine (25 mL) and stirred under argon at room temperature. 3,5-bis(trifluoromethyl)benzenesulfonyl chloride (4.05 g, 12.9 mmol) was added in portions, and the mixture stirred for 16 h. The solvent was evaporated, and the residue was purified by flash chromatography (silica gel, ethyl acetate/hexane) to give the title compound as a minor product. 1H NMR (250 MHz, CDCl3) δ8.60 (s, 4H), 8.21 (dd, 1H), 8.10 (s, 2H), 7.00-7.61 (m, 16H), 6.58 (d, 1H). The major product from this reaction was benzhydrol 2-[2-[3,5-bis(trifluoromethyl)phenylsulfonamido]-4-trifluoromethyl-phenoxy]benzoate.

Workup

  1. stirringthe mixture stirred for 16 h
  2. customThe solvent was evaporated
  3. customthe residue was purified by flash chromatography (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f906cc6fef0d403781668d7ec3c8f865
Source dataset
uspto-grants-1996_08
Patent number
US05545669

Reaction notes

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