Acetic Acid → 2-[(Benzenesulfonyl)methyl]-4-fluoro-1-nitrobenzene

HRID 2239985Notes

Reaction equation

HRID 2239985 reaction equation
Cl[CH2:2][S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])=[O:4].[F:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.CC(C)([O-])C.[K+].C(O)(=O)C>C1COCC1>[C:6]1([S:3]([CH2:2][C:17]2[CH:18]=[C:13]([F:12])[CH:14]=[CH:15][C:16]=2[N+:19]([O-:21])=[O:20])(=[O:5])=[O:4])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 9590p-FluoronitrobenzeneHCID 81625((Chloromethyl)sulphonyl)benzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 131807962-[(Benzenesulfonyl)methyl]-4-fluoro-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of chloromethylphenyl sulfone (10.51 g, 55.13 mmol) in THF (110 mL) was added 5.9 mL (56 mmol) of 1-fluoro-4-nitrobenzene. The reaction mixture was chilled to 0° C., and 1.0 M potassium tert-butoxide in THF (145 mL, 145 mmol) was added dropwise. The reaction mixture was stirred under nitrogen at ambient temperature for one hour. Acetic acid (9 mL, 160 mmol) was then added. The reaction mixture was solvent evaporated and partitioned in brine and ethyl acetate. The organic phase was then dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was stirred in diethyl ether, filtered and dried in vacuo at 73° C. for 12 hours. 2-Benzenesulfonylmethyl-4-fluoro-1-nitrobenzene as a light brown-yellow solid was obtained (10.24 g, 62.8%): MP: 169-171° C.; Mass spectrum (−EI, [M−H]−) m/z 294. 1HNMR (500 MHz, DMSO-d6): δ8.10-8.14 (m, 1H), 7.70-7.75 (m, 1H), 7.56-7.63 (m, 4H), 7.45-7.50 (m, 1H), 7.20 (dd, 1H, J=9.27 Hz and 2.81 Hz), 5.12 ppm (s, 2H). Elemental Analysis for C13H10FNO4S: Calcd: C, 52.88; H, 3.41; N, 4.74; Found: C, 52.63; H, 3.14; N, 4.66;

Workup

  1. customevaporated
  2. custompartitioned in brine
  3. dry with materialThe organic phase was then dried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. stirringThe residue was stirred in diethyl ether
  7. filtrationfiltered
  8. customdried in vacuo at 73° C. for 12 hours

Sources & evidence

ORD record
ord-0d629b013c664a3189d8e3925d4fc498
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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