p-Fluoronitrobenzene → HCID 14933055, compound

HRID 1030278

Reaction equation

HRID 1030278 reaction equation
CC([O-])(C)C.[K+].F[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.[Cl:17][CH2:18][CH2:19][CH2:20][SH:21]>CS(C)=O.O>[Cl:17][CH2:18][CH2:19][CH2:20][S:21][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 871343-ChloropropanethiolHCID 23665647Potassium tert-butoxide

Product 1

HCID 14933055HCID 14933055, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

To a cooled (10° C.), stirred suspension of KOtBu (8.9 g, 0.080 mol) in DMSO (40 mL) was added a solution of 4-fluoronitrobenzene (11.2 g, 0.080 mol) and 3-chloropropanethiol (8.8 g, 0.080 mol) in DMSO (40 mL) over 10 minutes. The mixture was stirred at room temperature for 3.5 hours, diluted with water (1000 ml), and extracted with ether. The extracts were washed with brine, dried (MgSO4), and concentrated. Purification by flash chromatography (10% EtOAc/hexane) gave 6.2 g (34%) of product as a yellow solid m.p. 45°-48° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 3.5 hours
  2. extractionextracted with ether
  3. washThe extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification by flash chromatography (10% EtOAc/hexane)

Sources & evidence

ORD record
ord-7e3d4cb3d6324a3a900fd6ef81d27707
Source dataset
uspto-grants-1992_04
Patent number
US05104892

Linked notes

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