Sodium hydride → HCID 86719001, compound

HRID 2280114Notes

Reaction equation

HRID 2280114 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])[CH:7]=[CH:6][C:5]=1[C:19](=[O:21])[CH3:20].[NH4+].[Cl-].[CH2:24]1COCC1.CS(C)=O>C1COCC1.CC(OC)(C)C>[Cl:3][C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])[CH:7]=[CH:6][C:5]=1[C:19]1([CH3:24])[CH2:20][O:21]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 21830753dimethylsulfoxide THFHCID 64335316HCID 64335316, compound

Product 1

HCID 86719001HCID 86719001, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

NaH (4.39 g) was suspended in THF/DMSO (400 mL) and Me3S—I (35.4 g) was added carefully in small portions. 30 min after completed addition, a solution of 1-[2-chloro-4-(2,4-difluorophenoxy)phenyl]ethanone (25 g) in 50 mL THF was added. After stirring overnight, the reaction mixture was diluted with MTBE and sat aq. NH4Cl-Sol was added. The organic phase was separated and the aqueous phase was three times extracted with MTBE (300 mL). the combined organic layers were washed with sat NaHCO3-solution, sat aq. NaCl and dried over Na2SO4. 2-[2-chloro-4-(2,4-difluorophenoxy)phenyl]-2-methyl-oxirane (23.5 g) was obtained as a brown oil and used in the next step without further purification. 1H-NMR (CDCl3; 400 MHz) (ppm)=1.65 (s, 3H); 2.8-3.0 (dd, 2H); 6.75-7.1 (m, 5H); 7.4 (d, 1H).

Workup

  1. additionMe3S—I (35.4 g) was added carefully in small portions
  2. custom30 min
  3. additionaddition
  4. additionwas added
  5. customThe organic phase was separated
  6. extractionextracted with MTBE (300 mL)
  7. washthe combined organic layers were washed with sat NaHCO3-solution
  8. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-8db8660ea50745e58d2489cf7c047010
Source dataset
uspto-grants-2015_09
Patent number
US09137996B2

Reaction notes

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