3-Chloro-4-fluoroaniline → HCID 59799399, compound

HRID 1891406Notes

Reaction equation

HRID 1891406 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:10]=[C:9]([C:11]([OH:13])=O)[O:8][N:7]=1.[Cl:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][C:21]=1[F:22])[NH2:18].P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1.C1(C)C=CC=CC=1>[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:10]=[C:9]([C:11]([NH:18][C:17]2[CH:19]=[CH:20][C:21]([F:22])=[C:15]([Cl:14])[CH:16]=2)=[O:13])[O:8][N:7]=1

Participants

6

Reactant 3

HCID 97083-Chloro-4-fluoroanilineHCID 24813Phosphorus oxychlorideHCID 58332202HCID 58332202, compound

Product 1

HCID 59799399HCID 59799399, compoundYield 387.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

A solution of 3-(3-bromopropoxy)isoxazole-5-carboxylic acid (130 mg, 0.054 mmol) and 3-chloro-4-fluoroaniline (78 mg, 0.054 mmol) in pyridine (2.0 mL) was stirred at room temperature until totally dissolved. The solution was cooled to −30° C. (acetonitrile/ice) and phosphoryl chloride (240 μL, 2.6 mmol) was added dropwise. The mixture was stirred for 1 h in the ice bath. The mixture was diluted with toluene before evaporation in vacuo. The crude was purified by reverse phase chromatography to give the desired product (79 mg, 39%). MF=C13H12BrClFN2O3; LCMS calculated for C13H12BrClFN2O3 (M+H)+: m/z=377.

Workup

  1. dissolutionuntil totally dissolved
  2. additionwas added dropwise
  3. customThe crude was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-78c4ed93002d49488441d990e235538d
Source dataset
uspto-grants-2013_08
Patent number
US08507541B2

Reaction notes

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