3-Fluoroaniline → HCID 86713659, compound

HRID 1257225Notes

Reaction equation

HRID 1257225 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Cl[C:10]([O:12][C:13]([CH3:15])=[CH2:14])=[O:11].C([O-])(O)=O.[Na+]>CCOC(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:10](=[O:11])[O:12][C:13]([CH3:15])=[CH2:14])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 97423-FluoroanilineHCID 93846Isopropenyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 86713659HCID 86713659, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

To a biphasic solution of 3-fluoroaniline (0.3 mL, 3.12 mmol) in 1:1 EtOAc/water (10 mL) was added isopropenyl chloroformate (0.564 g, 4.68 mmol) and NaHCO3 (1.31 g, 15.6 mmol) and the mixture stirred at RT overnight. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were concentrated to dryness and purified by silica gel chromatography (EtOAc/Hex) to furnish prop-1-en-2-yl 3-fluorophenylcarbamate (125 mg, 21% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.14 (s, 1H), 7.35 (m, 1H), 7.31 (m, 1H), 7.21 (m, 1H), 6.83 (m, 1H), 4.74 (m, 2H), 1.92 (s, 3H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. concentrationThe combined organic layers were concentrated to dryness
  4. custompurified by silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-71f711cc30934b7584d540f28543be33
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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