Benzyl Bromide → HCID 86652870, compound

HRID 241379Notes

Reaction equation

HRID 241379 reaction equation
[OH:1][N:2]=[C:3]([C:22]1[CH:34]=[CH:33][C:25]([O:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:24]([CH3:35])[CH:23]=1)[CH2:4][CH2:5][C:6]1[S:7][C:8]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:9]=2[C:10]=1[CH:11]([CH3:13])[CH3:12].[H-].[Na+].[CH2:38](Br)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[Cl-].[NH4+]>C1COCC1>[CH2:38]([O:1][N:2]=[C:3]([C:22]1[CH:34]=[CH:33][C:25]([O:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:24]([CH3:35])[CH:23]=1)[CH2:4][CH2:5][C:6]1[S:7][C:8]2[CH:17]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:15]=[CH:14][C:9]=2[C:10]=1[CH:11]([CH3:13])[CH3:12])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86652871HCID 86652871, compound

Product 1

HCID 86652870HCID 86652870, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold solution of ethyl 4-[1-hydroxyimino-3-[3-isopropyl-6-(trifluoromethyl)benzothiophen-2-yl]propyl]-2-methylphenoxyacetate [Example 16 (1)] (90 mg, 0.18 mmol) in THF (1.8 mL) was added 55% sodium hydride (12 mg, 0.27 mmol). The mixture was stirred for 10 minutes, to which was added benzyl bromide (0.03 mL, 0.3 mmol). The mixture was stirred for 72 hours at room temperature, treated with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/1), to give the titled compound as a colorless oil (25 mg, yield 24%).

Workup

  1. stirringThe mixture was stirred for 72 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/1)

Sources & evidence

ORD record
ord-22558c2cc94347a7a320a2553aff2be6
Source dataset
uspto-grants-2014_02
Patent number
US08648208B2

Reaction notes

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