Sodium sulfide nonahydrate → 3-Bromo-4-mercaptobenzonitrile

HRID 1817194Notes

Reaction equation

HRID 1817194 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[C:5]#[N:6].O.O.O.O.O.O.O.O.O.[S-2:20].[Na+].[Na+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[SH:20])[C:5]#[N:6]

Participants

4

Reactant 2

HCID 73972Sodium sulfide nonahydrateHCID 1235793-Bromo-4-fluorobenzonitrile

Product 1

HCID 200371753-Bromo-4-mercaptobenzonitrileYield 88.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3-Bromo-4-fluorobenzonitrile (100 g) was dissolved in dimethylformamide (DMF) (500 ml), and sodium sulfide nonahydrate (132 g) was added thereto at 0° C. and then stirred overnight at room temperature. The reaction mixture was poured to ice water (1 L) and the insoluble material was filtered off. The filtrate was added to a 1N aqueous hydrochloric acid solution (700 ml) under ice-cooling and the precipitate was collected by filtration. The crystals thus obtained were washed with hexane/diisopropyl ether and water and then dried to obtain 3-bromo-4-mercaptobenzonitrile (95.0 g) as a light-yellow solid.

Workup

  1. filtrationthe insoluble material was filtered off
  2. additionThe filtrate was added to a 1N aqueous hydrochloric acid solution (700 ml) under ice-
  3. temperaturecooling
  4. filtrationthe precipitate was collected by filtration
  5. customThe crystals thus obtained
  6. washwere washed with hexane/diisopropyl ether and water
  7. customdried

Sources & evidence

ORD record
ord-792a219277d54c5cb6eabe7d466eac83
Source dataset
uspto-grants-2009_10
Patent number
US07598240B2

Reaction notes

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