2-Bromopropane → HCID 21243558, compound

HRID 621792Notes

Reaction equation

HRID 621792 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[S:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14].[CH3:17][C:18](C)([O-])[CH3:19].[K+].BrC(C)C>CS(C)=O>[CH3:17][CH:18]([O:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[S:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14])[CH3:19]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 23665647Potassium tert-butoxideHCID 54710750Methyl 3-hydroxy-5-phenyl-2-thiophenecarboxylate

Product 1

HCID 21243558HCID 21243558, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 3-hydroxy-5-phenyl-2-thiophenecarboxylate (20.0 g, 85 mmoles) is dissolved in dimethylsulfoxide (80 mL) under argon and cooled in an ice bath. Potassium t-butoxide (10.1 g, 90 mmoles) is added, followed after 25 minutes by 2-bromopropane (22.1 g, 180 mmoles), and the ice bath is removed. After 24 hours the mixture is heated to 80° C. for 1 hour, then poured into ice water (500 mL), stirred, and acidified with concentrated HCl. The mixture is extracted with dichloromethane (3×200 mL) and the combined extracts are washed with brine, dried over MgSO4 and stripped of solvent under reduced pressure to leave the product as a syrupy residue (22.1 g) sufficiently pure for further use.

Workup

  1. temperaturecooled in an ice bath
  2. customthe ice bath is removed
  3. additionpoured into ice water (500 mL)
  4. extractionThe mixture is extracted with dichloromethane (3×200 mL)
  5. washthe combined extracts are washed with brine
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-3130bb487fbb4c9d95fc406c8d7ef3de
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

Loading…