Dichloromethane → HCID 15887504, compound

HRID 1602798Notes

Reaction equation

HRID 1602798 reaction equation
[P:1]([O:8][CH2:9][CH3:10])([O:5]CC)[O:2][CH2:3][CH3:4].Br[CH2:12][C:13]1[S:17][C:16]([C:18]([OH:20])=[O:19])=[CH:15][CH:14]=1.[OH-].[Na+].ClCCl>C(O)C>[CH2:9]([O:8][P:1]([CH2:12][C:13]1[S:17][C:16]([C:18]([OH:20])=[O:19])=[CH:15][CH:14]=1)([O:2][CH2:3][CH3:4])=[O:5])[CH3:10]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 31215Triethyl phosphiteHCID 158875035-(Bromomethyl)thiophene-2-carboxylic acid

Product 1

HCID 15887504HCID 15887504, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
160 °C

Procedure

189 g of triethyl phosphite was added to 84 g of 5-bromomethyl-2-thiophenecarboxylic acid obtained above, and the mixture was stirred with heating at 160° C. for 1 hour. The reaction mixture was dissolved in 200 ml of ethanol, and 190 ml of a 4N aqueous solution of sodium hydroxide was slowly added dropwise with ice-cooling and stirring. After stirring the resulting mixture at room temperature for 12 hours, 200 ml of dichloromethane was added for separating the reaction mixture. The obtained aqueous layer was mixed with 300 ml of a 30% aqueous solution of hydrochloric acid and subjected to extraction with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, giving 95 g of 5-[(diethoxyphosphoryl)methyl]-2-thiophenecarboxylic acid as colorless crystals having a melting point of 77-78° C.

Workup

  1. customobtained above, and the mixture
  2. temperaturecooling
  3. stirringstirring
  4. stirringAfter stirring the resulting mixture at room temperature for 12 hours
  5. customfor separating the reaction mixture
  6. additionThe obtained aqueous layer was mixed with 300 ml of a 30% aqueous solution of hydrochloric acid
  7. extractionsubjected to extraction with chloroform
  8. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  9. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-84168f89d59d40e49c52720f24063734
Source dataset
uspto-grants-1999_11
Patent number
US05985858

Reaction notes

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