Hydrochloric Acid → HCID 11515492, compound

HRID 1682341Notes

Reaction equation

HRID 1682341 reaction equation
[C:1]1([S:7]([CH:10]([F:12])[F:11])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.[OH-].[Na+].Cl>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].ClCCl>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]([OH:19])[C:10]([F:12])([F:11])[S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:9])=[O:8])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 77264-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 11816356((Difluoromethyl)sulfonyl)benzene

Product 1

HCID 11515492HCID 11515492, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A reaction mixture generated from 100 mg (0.52 mmol) of difluoromethyl phenyl sulfone, 225 mg (1.6 mmol) of 4-chlorobenzaldehyde, 1.5 mL of dichloromethane, 1 mL of 50% aqueous sodium hydroxide and 20 mg (0.050 mmol) of Aliquat 336 was poured into 20 mL of 1N HCl. Extraction of the aqueous mixture with three 10 mL portions of ethyl acetate followed by combination, drying (MgSO4), and concentration in vacuo of the organic layers gave a residue which was purified by preparative TLC (two 2 mm silica gel plates eluted with 10% ethyl acetate in toluene), affording 153 mg (88% yield) of 1-(4-chlorophenyl)-2,2-difluoro-2-phenylsulfonylethanol as a solid. Crystallization from toluene provided an analytical sample: mp; 100°-102° C.; IR (KBr) 3530, 3060, 2921, 1491, 1446, 1332, 1157, 1120, 1113, 1090, 1016, 1005, 784, 723, 683, 589, 538 cm-1 ; 1H NMR (CDCl3) δ 3.62 (broad s, 1H), 5.56 (dd, 1H, J=20, 3 Hz), 7.26-8.13 (m, 9H); 19F NMR (CDCl3, relative to CFCl3 -104.8 ppm (dd, 1F, JFF =238 Hz, JHF =3 Hz), -119.2 ppm (dd, 1F, JFF =238 Hz, JHF =20 Hz); mass spectrum (70 eV) m/e (relative intensity) 332 (9, M+), 143(44), 141(100, 77(33). Anal. Calcd. for C14H11ClF2O3S: C, 50.53; H, 3.33. Found: C, 50.49; H, 3.41.

Workup

  1. extractionExtraction of the aqueous mixture with three 10 mL portions of ethyl acetate
  2. customdrying
  3. concentration(MgSO4), and concentration in vacuo of the organic layers
  4. customgave a residue which
  5. customwas purified by preparative TLC (two 2 mm silica gel plates eluted with 10% ethyl acetate in toluene)

Sources & evidence

ORD record
ord-862f11298db444c0bfe0436d72747a14
Source dataset
uspto-grants-1992_12
Patent number
US05175302

Reaction notes

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