Borane → 2-[2-[3,5-Bis(trifluoromethyl)phenylsulfonamido]-4-trifluoromethylphenoxy]benzyl alcohol

HRID 1077991Notes

Reaction equation

HRID 1077991 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([S:13]([NH:16][C:17]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:18]=2[O:19][C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[C:22](O)=[O:23])(=[O:15])=[O:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.B>O1CCCC1>[F:37][C:2]([F:1])([F:38])[C:3]1[CH:4]=[C:5]([S:13]([NH:16][C:17]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:18]=2[O:19][C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[CH2:22][OH:23])(=[O:15])=[O:14])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 9808192SB 203347

Product 1

HCID 545192822-[2-[3,5-Bis(trifluoromethyl)phenylsulfonamido]-4-trifluoromethylphenoxy]benzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[2-[3,5-Bis(trifluoromethyl)phenylsulfonamido]-4-trifluoromethylphenoxy]benzoic acid (0.1 g, 0.17 mmol) was dissolved in tetrahydrofuran (5 mL) and stirred under argon at room temperature. A 1M solution of borane (0.5 mL, 0.5 mmol) was added and the mixture was stirred for 16 h. Evaporation of the solvent followed by aqueous workup and flash chromatography (silica gel, ethyl acetate/hexane); and then recrystallization provided the title compound as a white crystalline solid; mp 123°-125° C.

Workup

  1. stirringthe mixture was stirred for 16 h
  2. customEvaporation of the solvent
  3. customand then recrystallization

Sources & evidence

ORD record
ord-e8a92416eaaa4bada3bbd96af00a37b8
Source dataset
uspto-grants-1996_08
Patent number
US05545669

Reaction notes

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