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

HRID 847141Notes

Reaction equation

HRID 847141 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 51.5%

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 (51%) 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-c16a29ca82ae41b39fa7c27d993a5e57
Source dataset
uspto-grants-1992_08
Patent number
US05140026

Reaction notes

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