Hydrochloric Acid → 2-Bromo-4-chlorobenzene-1-thiol

HRID 992486Notes

Reaction equation

HRID 992486 reaction equation
[Br:1][C:2]12[S:10][CH:3]1[CH:4]=[CH:5][C:6]1([Cl:9])S[CH:7]12.[BH4-].[Na+].CO.Cl>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[SH:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 86586184HCID 86586184, compound

Product 1

HCID 218168372-Bromo-4-chlorobenzene-1-thiol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 2-bromo-4-chlorobenzene disulfide (3.8 g, 8.5 mmol) in THF (30 mL) was treated with NaBH4 (0.83 g, 22.0 mmol). The mixture was refluxed for a while and treated with MeOH (2 mL); heating was resumed for 0.5 hours. Mixture was cooled to 23° C., acidified with HCl (3N) and extracted with Et2O. The Et2O extracts were dried over MgSO4, filtered, and the filtrate was concentrated in vacuo to afford the title compound which was used without further purification.

Workup

  1. temperatureThe mixture was refluxed for a while
  2. temperatureheating
  3. extractionextracted with Et2O
  4. dry with materialThe Et2O extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-03e0bdca654d4eacb7e9d8b325fa90b4
Source dataset
uspto-grants-2002_10
Patent number
US06469042B1

Reaction notes

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