Ammonia → 2-Fluoro-4-thiocyanatoaniline
Reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[S-:9][C:10]#[N:11].[NH4+].BrBr.N.Br>C(O)(=O)C>[NH2:4][C:3]1[CH:5]=[CH:6][C:7]([S:9][C:10]#[N:11])=[CH:8][C:2]=1[F:1]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 22.2 g of 2-fluoroaniline in 100 mL of acetic acid is added 32 g of ammonium thiocyanate. The flask is immersed in an ice bath and the mixture stirred during the dropwise addition of 32 g of bromine in 40 mL of acetic acid. After the addition, which takes ca 40 min., the mixture is stirred for 1 h at 0° C. and them dumped into 700 mL of rapidly stirred icewater. Conc. aqueous ammonia is added to neutralize HBr and bring the pH of the mixture to 4.0. The resulting yellow solid is filtered, washed well with water, and dried in vacuo to provide 27.72 g of 4-amino-3-fluorobenzenesulfenyl cyanide as a pale yellow solid.
Workup
- customThe flask is immersed in an ice bath
- additionAfter the addition, which
- waittakes ca 40 min.
- filtrationThe resulting yellow solid is filtered
- washwashed well with water
- customdried in vacuo
Sources & evidence
- ORD record
- ord-99fdd52b547a4b21bc45d11d4729b69a
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06093732
Reaction notes
Loading…