1-Bromo-3-chloropropane → 1-[(3-Chloropropyl)sulfanyl]-4-nitrobenzene

HRID 2082068Notes

Reaction equation

HRID 2082068 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Na].Br[CH2:13][CH2:14][CH2:15][Cl:16]>CO>[Cl:16][CH2:15][CH2:14][CH2:13][S:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 158094-NitrobenzenethiolHCID 5360545Sodium

Product 1

HCID 149330551-[(3-Chloropropyl)sulfanyl]-4-nitrobenzeneYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

4-Nitrothiophenol (80%, 25.0 g, 129 mmol) was added to a solution formed by adding sodium (5.55 g, 242 mmol) to methanol (500 mL) maintained at 0° C. After 0.5 h the reaction was warmed to ambient temperature and 1-bromo-3-chloropropane (50.7 g, 322 mmol) was added in one portion. The reaction mixture was stirred overnight and filtered. The filtrate was reduced to half volume and the solid which formed was collected by filtration. Recrystallization from methanol afforded 15.4 g (52%) of yellow solid, mp 50°-52° C.

Workup

  1. customformed
  2. temperatureAfter 0.5 h the reaction was warmed to ambient temperature
  3. filtrationfiltered
  4. customthe solid which formed
  5. filtrationwas collected by filtration
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-dfb769ea2bdc48d8b1a0d69dd6095bc1
Source dataset
uspto-grants-1993_02
Patent number
US05187189

Reaction notes

Loading…