(Diethylamino)sulfur trifluoride → 1-Fluoro-4-{2-fluoro-2-[4-(phenylsulfonyl)phenyl]ethyl}benzene

HRID 2376981Notes

Reaction equation

HRID 2376981 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])=[CH:13][CH:12]=2)O)=[CH:4][CH:3]=1.C(N(S(F)(F)[F:32])CC)C.C(=O)([O-])O.[Na+]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([F:32])[C:11]2[CH:16]=[CH:15][C:14]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 210994432-(4-Fluorophenyl)-1-[4-(phenylsulfonyl)phenyl]ethanol

Product 1

HCID 210994021-Fluoro-4-{2-fluoro-2-[4-(phenylsulfonyl)phenyl]ethyl}benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-Fluorophenyl)-1-[4-(phenylsulfonyl)phenyl]ethanol (Example 118, 100 mg, 0.28 mmol) was dissolved in dichloromethane (5 mL) and (diethylamino)sulfur trifluoride (0.05 mL, 0.32 mmol) added. The reaction was stirred at room temperature for 30 minutes. Saturated sodium hydrogencarbonate was added and the products extracted into ethyl acetate. The organic layer was dried over MgSO4 and evaporated. The residue was triturated with diethyl ether/isohexane to give the title compound as a beige solid. δH (360 MHz, CDCl3): 7.94-7.90 (4H, m), 7.58-7.48 (3H, m), 7.35 (2H, d, J=8.5 Hz), 7.08-7.00 (2H, m), 6.96-6.90 (2H, m), 5.69-5.53 (1H, m), 3.21-2.99 (2H, m).

Workup

  1. extractionthe products extracted into ethyl acetate
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated
  4. customThe residue was triturated with diethyl ether/isohexane

Sources & evidence

ORD record
ord-f73d34719b884c0b88fb0f070f7beb2b
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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