Trifluoroacetic acid → 1-(2-((3-Fluorophenyl)methyl)phenyl)-4-(methylsulfonyl)benzene

HRID 49181Notes

Reaction equation

HRID 49181 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8](O)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O.[BH4-].[Na+]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 101552011-(2-((3-Fluorophenyl)hydroxymethyl)phenyl)-4-(methylsulfonyl)benzene

Product 1

HCID 99025211-(2-((3-Fluorophenyl)methyl)phenyl)-4-(methylsulfonyl)benzeneYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The product of the Example 25b (140 mg, 0.393 mmol) was dissolved in anhydrous dichloromethane (10 mL) and under nitrogen atmosphere was added trifluoroacetic acid (5 mL) at 0° C. The reaction mixture was stirred at 0° C. for 10 minutes and to the resulting dark orange solution was then added, in small portions sodium borohydride (290 mg, 7.86 mmol). The reaction mixture was stirred at 0° C. for 15 minutes and then at room temperature for 5 minutes. The solvent and trifluoroacetic acid were evaporated under reduced pressure and the residue was extracted with dichloromethane. The combined organic extracts were washed with water, brine, dried over sodium sulfate and filtered. The filtrate was evaporated under reduced pressure to give the crude which upon trituration with hexane yielded the title compound as a white solid, (110 mg, 83%), mp 97-98° C. 1H NMR (CDCl3) δ7.97 (d, J=8.3 Hz, 2H), 7.45 (d, J=8.3 Hz, 2H), 7.45-7.15 (m, 5H), 6.98 (dt, J=8.4 and 2.2 Hz, 1H), 6.75 (d, J=7.6 Hz, 1 H), 6.63 (d, J=10 Hz, 1H); 13C NMR (CDCl3) δ164.4, 161.2, 147.2, 143.3 (d, J=7 Hz), 140.3, 139.2, 137.2, 130.7, 130.1 (2×C), 129.9, 129.7 (d, J=2.5 Hz), 128.6, 127.1 (2×C), 126.9, 124.3 (d, J=2.5 Hz), 115.4 (d, J=21 Hz), 112.9 (d, J=21 Hz), 44.5, 38.9; LRMS (APIMS) m/z 358 (M+NH4)+.

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 15 minutes
  2. waitat room temperature for 5 minutes
  3. customThe solvent and trifluoroacetic acid were evaporated under reduced pressure
  4. extractionthe residue was extracted with dichloromethane
  5. washThe combined organic extracts were washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated under reduced pressure
  9. customto give the crude which upon trituration with hexane

Sources & evidence

ORD record
ord-04d8e7a459c24ee389770c785725c1fc
Source dataset
uspto-grants-2004_03
Patent number
US06706724B2

Reaction notes

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