2-Fluoroaniline → 2-Fluoro-4-thiocyanatoaniline

HRID 1949330Notes

Reaction equation

HRID 1949330 reaction equation
[S-:1][C:2]#[N:3].[Na+].[Br-].[Na+].BrBr.[F:9][C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12].C(=O)([O-])[O-].[Na+].[Na+]>O.CO>[F:9][C:10]1[CH:16]=[C:15]([S:1][C:2]#[N:3])[CH:14]=[CH:13][C:11]=1[NH2:12]

Participants

8

Reactant 5

HCID 95842-FluoroanilineHCID 10340Sodium CarbonateHCID 24408BromineHCID 253881Sodium BromideHCID 516871Sodium thiocyanate

Product 1

HCID 43563652-Fluoro-4-thiocyanatoaniline

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a mixed liquid of 210.9 g of sodium thiocyanate and 200.9 g of methanol was dropped a solution composed of 60.2 g of sodium bromide, 166.6 g of methanol and 163.7 g of bromine over 90 minutes while internal temperature was controlled at −10 to −6° C. To the mixed liquid was dropped 100.0 g of 2-fluoroaniline over 50 minutes while internal temperature was controlled at −10 to −5° C. The resulting mixture was stirred at the same temperature for 3 hours and then was poured into 784 g of water cooled to 0° C. The resulting mixture was neutralized with sodium carbonate and then was extracted twice with 196 g of chloroform. The organic layer was dried over magnesium sulfate and then concentrated, so that 151.9 g of 2-fluoro-4-thiocyanoaniline (Compound S-4) was obtained.

Workup

  1. customwas controlled at −10 to −6° C
  2. customwas controlled at −10 to −5° C
  3. extractionwas extracted twice with 196 g of chloroform
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated, so that 151.9 g of 2-fluoro-4-thiocyanoaniline (Compound S-4)
  6. customwas obtained

Sources & evidence

ORD record
ord-e968df1fb9dd41d7a66874b98dfa3860
Source dataset
uspto-grants-2013_03
Patent number
US08399707B2

Reaction notes

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