Acetic Acid → 2,3,4-Tribromo-5-(chloromethyl)thiophene

HRID 904462

Reaction equation

HRID 904462 reaction equation
C=O.[ClH:3].[Br:4][C:5]1[C:9]([Br:10])=[C:8]([Br:11])[S:7][CH:6]=1.[C:12](O)(=O)C>>[Cl:3][CH2:12][C:6]1[S:7][C:8]([Br:11])=[C:9]([Br:10])[C:5]=1[Br:4]

Participants

5

Conditions

Temperature
70 °C

Procedure

4.07 G. (50 mmol) of formalin (37%) and 40 ml. of concentrated hydrochloric acid were added to a solution of 10.2 g. (33.3 mmol) of 3,4,5-tribromothiophene in 20 ml. of acetic acid. The resulting mixture was warmed to 70° C. After 6 hrs., 4.07 g. of formalin were added and heating was continued overnight. The resulting mixture as cooled, poured on ice water and extracted with ether. The organic phase was washed twice with water, sodium bicarbonate and water, dried and evaporated to give crude 2-chloromethyl-3,4,5-tribromothiophene.

Workup

  1. temperatureheating
  2. waitwas continued overnight
  3. temperatureThe resulting mixture as cooled
  4. additionpoured on ice water
  5. extractionextracted with ether
  6. washThe organic phase was washed twice with water, sodium bicarbonate and water
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-af7cde1149be4bb3b7c2aec59249a2f8
Source dataset
uspto-grants-1980_10
Patent number
US04230872

Linked notes

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