4'-Fluoroacetophenone → HCID 16741950, compound

HRID 1394628Notes

Reaction equation

HRID 1394628 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][SH:3].[H-].[Na+].F[C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=1>CN(C=O)C.C(OCC)(=O)C>[CH3:6][O:5][C:1](=[O:4])[CH2:2][S:3][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 98284'-FluoroacetophenoneHCID 16907Methyl ThioglycolateHCID 24758Sodium hydride

Product 1

HCID 16741950HCID 16741950, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Methyl thioglycolate was dissolved in DMF (10 ml) and this mixture was cooled to 0° C. under an atmosphere of nitrogen. NaH (750 mg of 60% mineral oil dispersion, 18.1 mmol) was then added in one portion. After 5 min., the ice bath was removed and p-fluoroacetophenone (1 ml, 8.2 mmol) was added in one portion. The reaction mixture stirred at ambient temperature for 1 hr then diluted with ethyl acetate (50 ml) and washed with water. The aqueous layer was extracted with ethyl acetate (2×50 ml) and the combined organics dried over MgSO4 and concentrated in vacuo to yield (4-acetyl-phenylsulfanyl)-acetic acid methyl ester, as a white waxy solid (1.48 g, 80%). 1H NMR (250 MHz, CDCl3): δ 7.80 (d, 2H, J=9.4), 7.32 (d, 2H, J=9.4), 3.71 (s, 2H), 3.67 (s, 3H), 2.50 (s, 3H). MS [EI+] 225 (M+H)+.

Workup

  1. customthe ice bath was removed
  2. washwashed with water
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×50 ml)
  4. dry with materialthe combined organics dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-62fac8616bc94344a1c1dff01de24a76
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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