Quinone → 2-(4-Fluorobenzenesulfonyl)benzene-1,4-diol

HRID 1006720Notes

Reaction equation

HRID 1006720 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[C:11]1(=[O:18])[CH:16]=[CH:15][C:14](=[O:17])[CH:13]=[CH:12]1>O.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:16]2[CH:15]=[C:14]([OH:17])[CH:13]=[CH:12][C:11]=2[OH:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4650QuinoneHCID 421250Sodium 4-fluorobenzene sulfinate

Product 1

HCID 223448682-(4-Fluorobenzenesulfonyl)benzene-1,4-diol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the title A compound, 4-fluorobenzenesulfinic acid (3 g, 18.75 mmol) in 10 mL of water is added to a solution of 1,4 benzoquinone (1.93 g, 17.86 mmol) in 30 mL of CH2Cl2 at RT. After 4 h, the precipitated product is collected by vacuum filtration and washed with cold CH2Cl2 and dried under vacuum to afford 2-(4-fluorobenzenesulfonyl)-benzene-1,4-diol: NMR (DMSO-d6) 6.73 (d, 1H, J=9), 6.92 (dd, 1H, J=9, 3), 7.31 (d, 1H, J=3),7.41 (app t, 2H, J=9), 7.96 (dd, 2H, J=9, 5), 9.41 (s, 1H), 10.05 (s, 1H); ESI-MS 267 [M-1]−.

Workup

  1. filtrationthe precipitated product is collected by vacuum filtration
  2. washwashed with cold CH2Cl2
  3. customdried under vacuum

Sources & evidence

ORD record
ord-b9d25962558643e3a0dbafae665a6a14
Source dataset
uspto-grants-2004_09
Patent number
US06790978B2

Reaction notes

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