1-Fluoro-4-[(4-nitrophenyl)sulfonyl]benzene → BENZENAMINE, 4-[(4-FLUOROPHENYL)SULFONYL]-

HRID 1795784Notes

Reaction equation

HRID 1795784 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O>CO.[Rh]>[F:19][C:16]1[CH:17]=[CH:18][C:13]([S:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)(=[O:12])=[O:11])=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 221793631-Fluoro-4-[(4-nitrophenyl)sulfonyl]benzene

Product 1

HCID 572814BENZENAMINE, 4-[(4-FLUOROPHENYL)SULFONYL]-

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-fluorophenyl 4-nitrophenyl sulfone (1.89 g, 6.72 mmol) in methanol (80 mL) is treated with Rhodium on carbon (5%, 95 mg) and hydrogenated at 20 psi for 24 hr. The mixture is filtered, rinsing with methylene chloride (2×100 mL) and methanol (100 mL). The filtrate is concentrated to near dryness and refiltered, rinsing with minimal methanol. The solid is dried in the vacuum oven at 500 to give the desired amine, mp=204–205°: IR (drift) 3473, 3373, 1638, 1592, 1489, 1303, 1294, 1285, 1231, 1159, 1144, 1107, 834, 713 and 689 cm−1; NMR (300 MHz, CDCl3) 7.80–7.95, 7.60–7.75, 7.13, 6.60–6.75 and 4.17 δ; MS (EI) m/z 251 (M+), 140, 108, 95, 92, 80, 65, 65, 63 and 51.

Workup

  1. filtrationThe mixture is filtered
  2. washrinsing with methylene chloride (2×100 mL) and methanol (100 mL)
  3. concentrationThe filtrate is concentrated
  4. washrinsing with minimal methanol
  5. customThe solid is dried in the vacuum oven at 500

Sources & evidence

ORD record
ord-913f6153aad24f5c9468b43c8927d2bf
Source dataset
uspto-grants-2006_04
Patent number
US07030109B2

Reaction notes

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