2-Fluoroaniline → HCID 18929217, compound

HRID 1599823Notes

Reaction equation

HRID 1599823 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[F:13][C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH2:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[F:13][C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH:16][CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4]

Participants

6

Reactant 3

HCID 95842-FluoroanilineHCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetate

Product 1

HCID 18929217HCID 18929217, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The procedure of Zahler et al. was followed with minor modification (Zahler, R.; Koster, W. H.; Slusarchyk, W. A. EP 0138407). To a solution of benzyl bromoacetate (18.0 g, 12.5 mL, 79.6 mmol) and o-fluoroaniline (8.8 g, 7.7 mL, 100 mol %), in anhydrous DMF (60 mL) was added anhydrous K2CO3 (11 g, 100 mol %), and the mixture was stirred at rt overnight. The reaction mixture was diluted with water (120 mL) and extracted with EtOAc (3×200 mL). The combined organic layer was washed with water, dried, and then concentrated. Purification by LPLC (5% EtOAc- hexane) provided 18.0 g (88%) of the title compound as a colorless oil: 1H NMR (CDCl3) δ7.39-7.35 (m, 5H), 7.03-6.97 (m, 2H), 6.72-6.67 (m, 1H), 6.59 (dt, J=8.4, J=1.2, 1H), 5.23 (s, 2H), 4.01 (s, 2H); 13C (CDCl3) δ170.59, 151.66 (d, J=240), 135.24, 128.64 (2 carbons), 128.52, 128.39 (2 carbons), 124.55 (d, J=3.5), 117.79 (d, J=7.1), 114.71 (d, J=17.7), 112.28 (d, J=3.5), 67.11, 45.54; MS (EI, m/z)259 (M+).

Workup

  1. extractionextracted with EtOAc (3×200 mL)
  2. washThe combined organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customPurification by LPLC (5% EtOAc- hexane)

Sources & evidence

ORD record
ord-5dc9c0e13dd64586a1b5a116292d3870
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

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