3-Fluoroaniline → (4-Fluoro-phenyl)-(3-fluoro-phenylamino)-acetic acid

HRID 1255043Notes

Reaction equation

HRID 1255043 reaction equation
Br[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[F:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17]>C(#N)C.CCOC(C)=O>[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH:2]([NH:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:14]([F:13])[CH:15]=2)[C:3]([OH:5])=[O:4])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 97423-Fluoroaniline2×HCID 16217752Bromo(4-fluorophenyl)acetic acid

Product 1

HCID 54890833(4-Fluoro-phenyl)-(3-fluoro-phenylamino)-acetic acidYield 90.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromo-2-(4-fluorophenyl)acetic acid (500 mg, 2.15 mmol) and 3-fluoroaniline (477 mg, 4.29 mmol) in acetonitrile (8 mL) is heated under microwave irradiation at 100° C. for 50 minutes. Then 3-fluoroaniline (238 mg, 2.15 mmol) is added again and reaction is heated at 120° C. for 45 minutes in a microwave oven (LC-MS monitoring: complete conversion). The organic solution is diluted with EtOAc and washed with 2N HCl and then with brine. The organic phase is dried over Na2SO4, filtered and the solvent is evaporated to give intermediate I131 as a white solid (510 mg, 90% yield).

Workup

  1. customreaction
  2. temperatureis heated at 120° C. for 45 minutes in a microwave oven (LC-MS monitoring: complete conversion)
  3. washwashed with 2N HCl
  4. dry with materialThe organic phase is dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent is evaporated

Sources & evidence

ORD record
ord-b2b10f18a5d24534ade0cf8d1d4c6ec9
Source dataset
uspto-grants-2013_06
Patent number
US08455646B2

Reaction notes

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