Acetyl chloride → HCID 14390561, compound

HRID 2231280Notes

Reaction equation

HRID 2231280 reaction equation
[Br:1][C:2]([Br:16])=[CH:3][C:4]1[S:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1.C(N(CC)CC)C.[C:24](Cl)(=[O:26])[CH3:25]>O1CCCC1.C(OCC)C>[Br:16][C:2]([Br:1])=[CH:3][C:4]1[S:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:24](=[O:26])[CH3:25])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14390560HCID 14390560, compound

Product 1

HCID 14390561HCID 14390561, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 2-(2,2-dibromoethenyl)-5-(4-hydroxyphenyl)thiophene (1.0 g, 0.003 mole) and triethylamine (1.2 g, 0.08 mole) in tetrahydrofuran (20 mL) was added acetyl chloride (0.44 g, 0.0056 mole). The reaction mixture was stirred at room temperature for approximately 18 hours. The mixture was diluted with diethyl ether and washed in succession with an aqueous 5% sodium hydroxide solution, water, and an aqueous saturated sodium chloride solution. The washed mixture was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure, yielding 0.5 g of 2-(2,2-dibromoethenyl)-5-(4-acetyloxyphenyl)thiophene as a solid (mp 115°-115.5° C.).

Workup

  1. washwashed in succession with an aqueous 5% sodium hydroxide solution, water
  2. dry with materialThe washed mixture was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-38426c50468d4231b5778056fe5d09bf
Source dataset
uspto-grants-1988_11
Patent number
US04782079

Reaction notes

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