Water → HCID 89443894, compound

HRID 1771615Notes

Reaction equation

HRID 1771615 reaction equation
[F:1][C:2]1[C:12]([NH:13][CH2:14][C:15]2[CH:20]=[C:19]([O:21]C)[CH:18]=[C:17]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[C:16]=2[F:30])=[C:11]([F:31])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([O-:8])=[O:7].[Al+3].[Cl-].[Cl-].[Cl-].[CH2:36](S)[CH3:37].O>C(Cl)Cl>[F:1][C:2]1[C:12]([NH:13][CH2:14][C:15]2[CH:20]=[C:19]([OH:21])[CH:18]=[C:17]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[C:16]=2[F:30])=[C:11]([F:31])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:36][CH3:37])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 131734658HCID 131734658, compound

Product 1

HCID 89443894HCID 89443894, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[2,4-difluoro-3-[[2-fluoro-3-(3-fluorophenyl)-5-methoxy-phenyl]methylamino]phenoxy]acetate (150 mg, 0.32 mmol, 1.0 eq) and AlCl3 (259 mg, 1.94 mmol, 6.0 eq) in CH2Cl2 (5 mL) at 0° C. was added ethanethiol (120 mg, 1.94 mmol, 6.0 eq). The reaction mixture was stirred at 0° C. for 3 h. The resulting mixture was poured into water and extracted with CH2Cl2. The organic extract was dried (Na2SO4), filtered and evaporated in vacuo and the residue purified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:2) to give the title as a yellow oil (120 mg, 82%).

Workup

  1. extractionextracted with CH2Cl2
  2. extractionThe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customthe residue purified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:2)

Sources & evidence

ORD record
ord-c40634898fcd42ec8e2bdb3b3011bacd
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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