Aniline → HCID 54889983, compound

HRID 77058Notes

Reaction equation

HRID 77058 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4](Br)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[F:11].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(C(C)C)C(C)C)C>C(#N)C>[CH3:1][O:2][C:3](=[O:13])[CH:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[F:11])[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 18004644Methyl 2-bromo-2-(2-fluorophenyl)acetate

Product 1

HCID 54889983HCID 54889983, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of bromo-(2-fluoro-phenyl)-acetic acid methyl ester (I259) (1.47 g, 5.95 mmol), aniline (814 ul, 8.93 mmol) and N-ethyl-N-isopropylpropan-2-amine (1.53 mL, 8.93 mmol) in acetonitrile (10 mL) is heated under microwave irradiation at 100° C. for 1 hour. The solvent is evaporated, the residue is taken up with DCM and washed with water and brine, dried over Na2SO4 and evaporated to afford intermediate I262 as a dark brown oil (1.54 g, quantitative yield).

Workup

  1. customThe solvent is evaporated
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-cff5276009a844bb9f17672e8e56bc48
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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