Sodium hydride → 2-(5-Bromothiophen-2-yl)-2-[(4-chlorophenoxy)methyl]oxirane

HRID 1982407Notes

Reaction equation

HRID 1982407 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)C.[Cl:8][C:9]1[CH:24]=[CH:23][C:12]([O:13][CH2:14][C:15]([C:17]2[S:21][C:20]([Br:22])=[CH:19][CH:18]=2)=[O:16])=[CH:11][CH:10]=1>CS(C)=O>[Br:22][C:20]1[S:21][C:17]([C:15]2([CH2:14][O:13][C:12]3[CH:11]=[CH:10][C:9]([Cl:8])=[CH:24][CH:23]=3)[CH2:4][O:16]2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 2444863HCID 2444863, compound

Product 1

HCID 133911832-(5-Bromothiophen-2-yl)-2-[(4-chlorophenoxy)methyl]oxirane

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

1.5 g (0.05 mol) of 80% strength sodium hydride are added in portions to a suspension of 11 g (0.05 mol) of trimethylsulphonium iodide in 100 ml of dimethyl sulphoxide under a nitrogen atmosphere, and the mixture is stirred for a further 30 minutes at room temperature. A solution of 15.5 g (0.046 mol) of 2-bromo-thien-5-yl 4-chlorophenoxymethyl ketone in a small amount of dimethyl sulphoxide is then added dropwise, and the mixture is heated to 6O° C. for 1 hour. The reaction mixture is then poured onto water, and extracted with methylene chloride. The organic phase is washed several times with water, dried over magnesium sulphate and evaporated down. Crude 2-(2-bromo-thien-5-yl)-2-(4-chlorophenoxymethyl)-oxirane is obtained as a viscous oil, which is directly reacted further. ##STR9##

Workup

  1. temperaturethe mixture is heated to 6O° C
  2. waitfor 1 hour
  3. additionThe reaction mixture is then poured onto water
  4. extractionextracted with methylene chloride
  5. washThe organic phase is washed several times with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated down

Sources & evidence

ORD record
ord-3fb829bd77744718ba11979316f97c9f
Source dataset
uspto-grants-1986_06
Patent number
US04596815

Reaction notes

Loading…