2-Fluoroaniline → 2-Fluoro-4-thiocyanatoaniline

HRID 1905445Notes

Reaction equation

HRID 1905445 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].[Na+].BrBr.[Br-].[Na+].C(=O)([O-])O.[Na+]>CO.O>[F:1][C:2]1[CH:8]=[C:7]([S:9][C:10]#[N:11])[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

8

Reactant 5

HCID 95842-FluoroanilineHCID 24408Bromine2×HCID 253881Sodium BromideHCID 516871Sodium thiocyanateHCID 516892Sodium Bicarbonate

Product 1

HCID 43563652-Fluoro-4-thiocyanatoanilineYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To 550 ml of methanol were added 111 g of 2-fluoroaniline and 240 g of sodium thiocyanate, and the mixture was cooled to 0° C. A cooled (0° C.) solution of 176 g of bromine in 500 ml of methanol saturated with sodium bromide was added dropwise to the mixture, with stirring, over the period of 1 hour 15 minutes, during which cooling was effected to maintain the internal temperature at not more than 3° C. After the addition of bromine was completed, the reaction mixture was poured in 2 l of cold water, and 100 g of sodium hydrogencarbonate was added to make the mixture weakly alkaline. The crystals, which separated out, were recovered by filtration and washed with cold water to give 144.5 g of crude 2-fluoro-4-thiocyanatoaniline.

Workup

  1. additionwas added dropwise to the mixture
  2. temperaturecooling
  3. temperatureto maintain the internal temperature at not more than 3° C
  4. customThe crystals, which separated out
  5. filtrationwere recovered by filtration
  6. washwashed with cold water

Sources & evidence

ORD record
ord-0509de6d237244c490be51ee9a080a32
Source dataset
uspto-grants-1989_06
Patent number
US04843100

Reaction notes

Loading…