(Diethylamino)sulfur trifluoride → HCID 14291997, compound

HRID 359210Notes

Reaction equation

HRID 359210 reaction equation
C(N(S(F)(F)[F:7])CC)C.C(=O)=O.CC(C)=O.[F:17][C:18]([F:37])([S:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=[O:30])=[O:29])[CH:19]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)O>ClCCl>[CH3:27][C:24]1[CH:25]=[CH:26][C:21]([CH:19]([F:7])[C:18]([S:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:30])=[O:29])([F:37])[F:17])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 14291991HCID 14291991, compoundHCID 18522661Acetone cardice

Product 1

HCID 14291997HCID 14291997, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.24 mL (1.8 mmol) of diethylaminosulfur trifluoride in 5 mL of dichloromethane was cooled to -78° C. (dry ice-acetone bath) and treated dropwise with a solution of 0.50 g (1.6 mmol) of 2,2-difluoro-1-(4-methylphenyl)-2-phenylsulfonylethanol in 2 mL of dichloromethane. The cooling bath was removed, and 30 minutes later 2 mL of saturated NaHCO3 was added with vigorous stirring. The organic layer was removed, washed with one 2 mL portion of water, dried (MgSO4), and concentrated in vacuo to give a residue which was crystallized from toluene-hexane, affording 0.36 g (71% yield) of 2-(4-methylphenyl)-1-phenylsulfonyl-1,1,2-trifluoroethane; mp 80°-82° C.; IR (KBr) 2924, 1447, 1352, 1185, 1163, 1117, 1054, 1013, 787, 757, 720, 686, 603, 567, 533, cm--1 ; lHNMR (CDCl3) δ2.36 (s, 3H), 6.10 (ddd, lH, JHF = 44, 18, 5 Hz), 7.16-8.07 (m, 9H); 19F NMR (CDCl3, relative to CFCl3)-44.0 ppm (dt, IF J=44, 16 Hz)-109.3 ppm (dd, lF, J=247, 15 Hz),-118.8 ppm (dt, IF, J=248, 17 Hz); mass spectrum (70 eV) m/e (relative intensity) 314 (11, M+), 172 (41), 123 (100), 77 (31). Anal. Calcd. for C15H13F3O2S: C, 57.32; H, 4.17. Found: C, 56.90; H, 4.47.

Workup

  1. customThe cooling bath was removed
  2. addition30 minutes later 2 mL of saturated NaHCO3 was added with vigorous stirring
  3. customThe organic layer was removed
  4. washwashed with one 2 mL portion of water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give a residue which
  8. customwas crystallized from toluene-hexane

Sources & evidence

ORD record
ord-8a74fa3b02d44705b8366b303f97fc1b
Source dataset
uspto-grants-1991_03
Patent number
US04999429

Reaction notes

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