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

HRID 897153Notes

Reaction equation

HRID 897153 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 50° 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 50°

Sources & evidence

ORD record
ord-37e330c01788412ca8c9765080080979
Source dataset
uspto-grants-2005_07
Patent number
US06921823B2

Reaction notes

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