Hydrochloric Acid → 5-Bromo-3-(2-chloro-ethyl)-thiophene-2-carbonyl chloride

HRID 69505Notes

Reaction equation

HRID 69505 reaction equation
[Br:1][C:2]1[S:11][C:5]2[C:6](=O)O[CH2:8][CH2:9][C:4]=2[CH:3]=1.[OH-:12].[Li+].[ClH:14].S(Cl)([Cl:17])=O>C1COCC1.O.CO.C1(C)C=CC=CC=1>[Br:1][C:2]1[S:11][C:5]([C:6]([Cl:14])=[O:12])=[C:4]([CH2:9][CH2:8][Cl:17])[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 24386Thionyl ChlorideHCID 689922162-Bromo-4,5-dihydro-thieno[2,3-c]pyran-7-one

Product 1

HCID 866351075-Bromo-3-(2-chloro-ethyl)-thiophene-2-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of 2-Bromo-4,5-dihydro-thieno[2,3-c]pyran-7-one (400 mg), Lithium hydroxide (246.7 mg) in THF/water/methanol (1.7 mL/1.7 mL/0.2 mL) was stirred for 6 h at room temperature. Then the reaction mixture was acidified with 2 N HCl and the aqueous phase was extracted with ethyl acetate, dried over sodium sulfate and the solvent removed. The obtained crude product was heated to reflux with thionylchloride (6.2 mL) for 2 h. Toluene was added and the volatile components removed in vacuum. This step was repeated twice.

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customthe solvent removed
  4. customThe obtained crude product
  5. temperaturewas heated
  6. customthe volatile components removed in vacuum

Sources & evidence

ORD record
ord-1417653a73c04630b7daef51b2b559c0
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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