N-bromobutanimide → HCID 19611696, compound

HRID 1602379Notes

Reaction equation

HRID 1602379 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[C:5]([CH3:11])=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:11][C:5]1[C:6]2[CH:7]=[CH:8][O:9][C:10]=2[C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 19611698HCID 19611698, compound

Product 1

HCID 19611696HCID 19611696, compoundYield 51.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 7-chloro-4-methyl-benzofuran (CAS-number 79444-976; 51.9 g), N-bromosuccinimide (61.4 g), benzoyl peroxide (0.52 g) and carbon tetrachloride (1200 ml) was heated under reflux under the illumination of an 80 W flood lamp for 20 h. The mixture was cooled, and filtered and the filtrate evaporated to dryness. The residue was absorbed onto silica and purified by chromatography on silica using ethyl acetate and hexane (1:20) to give the title compound (39.50 g) as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under the illumination of an 80 W flood lamp for 20 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. customthe filtrate evaporated to dryness
  6. customThe residue was absorbed onto silica
  7. custompurified by chromatography on silica

Sources & evidence

ORD record
ord-9919571e6aea444d8b4e0ad277d78b28
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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