Water → HCID 53396028, compound

HRID 1092258Notes

Reaction equation

HRID 1092258 reaction equation
C1(P(=[CH:20][C:21]([O:23][CH3:24])=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:25][C:26]1[S:30][C:29]([CH:31]=O)=[CH:28][CH:27]=1.O>C1(C)C=CC=CC=1>[Br:25][C:26]1[S:30][C:29]([CH:31]=[CH:20][C:21]([O:23][CH3:24])=[O:22])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 784285-Bromothiophene-2-carbaldehyde

Product 1

HCID 53396028HCID 53396028, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

4.2 g (12.5 mmol, 1.2 eq) of methyl triphenylphosphoranylideneacetate are added to a solution of 2.0 g (10.4 mmol, 1.0 eq) of 5-bromothiophene-2-carbaldehyde in 15 mL of toluene. The reaction mixture is stirred for 1 hour at 80° C. The reaction is stopped by adding 20 ml of water and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (80/20 heptane/ethyl acetate). 2.1 g of methyl 3-(5-bromothiophen-2-yl)acrylate are obtained. Yield=82%.

Workup

  1. extractionis then extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. customthe residue is then chromatographed on silica gel (80/20 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-89128080b8494469824f91440eb4e995
Source dataset
uspto-grants-2012_03
Patent number
US08129416B2

Reaction notes

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