Water → 4-(3-Allyloxy-5-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester

HRID 723040Notes

Reaction equation

HRID 723040 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7](Br)[CH:8]=[CH2:9].[CH3:11][O:12][C:13]([C:15]1[S:16][C:17]([S:31][CH3:32])=[C:18]([S:20]([C:23]2[CH:28]=[C:27]([OH:29])[CH:26]=[C:25]([Br:30])[CH:24]=2)(=[O:22])=[O:21])[CH:19]=1)=[O:14].O>CN(C=O)C.CCOC(C)=O>[CH3:11][O:12][C:13]([C:15]1[S:16][C:17]([S:31][CH3:32])=[C:18]([S:20]([C:23]2[CH:24]=[C:25]([Br:30])[CH:26]=[C:27]([O:29][CH2:9][CH:8]=[CH2:7])[CH:28]=2)(=[O:21])=[O:22])[CH:19]=1)=[O:14]

Participants

7

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 210571774-(3-Bromo-5-hydroxy-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 695867464-(3-Allyloxy-5-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cesium carbonate (33 mg, 0.1 mmol) and allylbromide (30 μL, 0.35 mmol) were added to a solution of 4-(3-bromo-5-hydroxy-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester ((Example 12: step d) 30 mg, 0.71 mmol) dissolved in dry DMF (3 mL). After stirring for 16 h at rt, the solution was poured into a mixture of water (20 mL) and EtOAc (30 mL). The layers were separated and the organic layer was extracted with water (5×5 mL), brine (20 mL), and was dried over sodium sulfate. The solvent was removed in vacuo to yield the title compound, which was used without further purification.

Workup

  1. customThe layers were separated
  2. extractionthe organic layer was extracted with water (5×5 mL), brine (20 mL)
  3. dry with materialwas dried over sodium sulfate
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-55f8604ddd0d4661b9c873930368db13
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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