Water → Isopropyl 2-[3-[[3-(3-fluorophenyl)-5-hydroxy-phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate

HRID 1771814Notes

Reaction equation

HRID 1771814 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH2:16][NH:17][C:18]3[C:19]([CH3:33])=[C:20]([CH:29]=[CH:30][C:31]=3[CH3:32])[O:21][CH2:22][C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[CH:11]=[C:12]([O:14]C)[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.C(S)C.[Al+3].[Cl-].[Cl-].[Cl-].O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH2:16][NH:17][C:18]3[C:19]([CH3:33])=[C:20]([CH:29]=[CH:30][C:31]=3[CH3:32])[O:21][CH2:22][C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[CH:11]=[C:12]([OH:14])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 89443955Isopropyl 2-[3-[[3-(3-fluorophenyl)-5-methoxy-phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate

Product 1

HCID 89443953Isopropyl 2-[3-[[3-(3-fluorophenyl)-5-hydroxy-phenyl]methylamino]-2,4-dimethyl-phenoxy]acetateYield 50,793.301%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of isopropyl 2-[3-[[3-(3-fluorophenyl)-5-methoxy-phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate (390 mg, 0.9 mmol, 1.0 eq) in CH2Cl2 (10 mL) at 0° C. was added dropwise ethyl mercaptan (321 mg, 5.2 mmol, 6.0 eq) and AlCl3 (690 mg, 5.2 mmol, 6.0 eq). The reaction mixture was stirred at room temperature for 1 h then poured into water and extracted with EtOAc. The organic extract was washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether: EtOAc, 100:1 to 10:1) to give the title compound as a white solid (200 g, 53%).

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue obtained
  8. customwas purified by column chromatography (petroleum ether: EtOAc, 100:1 to 10:1)

Sources & evidence

ORD record
ord-a35acdfe860a4d579f32501b6e7db24f
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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