Bromine → HCID 23343672, compound

HRID 27175Notes

Reaction equation

HRID 27175 reaction equation
[C:1]1(=[O:21])[N:5]([CH2:6][C:7]2[S:8][C:9]([C:12](=[O:15])[CH2:13][CH3:14])=[CH:10][CH:11]=2)[C:4](=[O:16])[C:3]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:2]12.[Br:22]Br>C(Cl)Cl>[Br:22][CH:13]([CH3:14])[C:12]([C:9]1[S:8][C:7]([CH2:6][N:5]2[C:4](=[O:16])[C:3]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:2]3[C:1]2=[O:21])=[CH:11][CH:10]=1)=[O:15]

Participants

4

Reactant 2

HCID 24408BromineHCID 233436752-Phthalimidomethyl-5-propionylthiophene

Product 1

HCID 23343672HCID 23343672, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Phthalimidomethyl-5-propionylthiophene (39.3 g., 0.13 mole) is dissolved in methylene chloride 300 ml.) and bromine (20.8 g., 0.13 mole) is added dropwise with stirring over 3/4 hours at room temperature. The solution is partially evaporated in vacuo to remove the hydrogen bromide. Then it is washed with saturated sodium carbonate solution and with water, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. This affords 5-(2-bromopropionyl)-2-(phthalimidomethyl) thiophene as a pale beige solid (46.7 g.), m.p. 127°-130° C.

Workup

  1. customThe solution is partially evaporated in vacuo
  2. customto remove the hydrogen bromide
  3. washThen it is washed with saturated sodium carbonate solution and with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a555335c3d247efa8cafe6e3ea787c1
Source dataset
uspto-grants-1980_09
Patent number
US04220654

Reaction notes

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