N-bromobutanimide → 3-[3-(Bromomethyl)phenyl]thiophene

HRID 2295847Notes

Reaction equation

HRID 2295847 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:13][CH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 4130346HCID 4130346, compound

Product 1

HCID 132459263-[3-(Bromomethyl)phenyl]thiopheneYield 61.4%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalyst2×HCID 5943Carbon TetrachlorideSolvent

Procedure

A stirred solution of 9.8 g (0.056 mol) of 3-(3-methylphenyl)thiophene in 250 mL of carbon tetrachloride was heated to reflux, and 0.5 g of benzoyl peroxide was added. Heating was continued, and after five minutes an additional 0.5 g of benzoyl peroxide and 10 g of N-bromosuccinimide were added. Upon complete addition, the reaction mixture was heated under reflux for an additional 2.5 hours, then cooled in an ice-water bath for one hour. The reaction mixture was filtered, and the filter cake washed with 50 mL of carbon tetrachloride. The wash and filtrate were combined, and the whole was washed with 200 mL of a saturated aqueous solution of sodium chloride. The organic layer was dried with magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to give a residual oil. The residual oil was subjected to distillation under reduced pressure using a Kugelrohr distilling system to give 8.7 g of 3-(3-bromomethylphenyl)thiophene, b.p. 95°-150° C./0.1 mm.

Workup

  1. temperatureto reflux
  2. temperatureHeating
  3. additionUpon complete addition
  4. temperaturethe reaction mixture was heated
  5. temperatureunder reflux for an additional 2.5 hours
  6. temperaturecooled in an ice-water bath for one hour
  7. filtrationThe reaction mixture was filtered
  8. washthe filter cake washed with 50 mL of carbon tetrachloride
  9. washThe wash
  10. washthe whole was washed with 200 mL of a saturated aqueous solution of sodium chloride
  11. dry with materialThe organic layer was dried with magnesium sulfate
  12. filtrationfiltered
  13. concentrationthe filtrate concentrated under reduced pressure
  14. customto give a residual oil
  15. distillationThe residual oil was subjected to distillation under reduced pressure
  16. distillationdistilling system

Sources & evidence

ORD record
ord-fdd73c85a7e34a248060b13d2963e64c
Source dataset
uspto-grants-1984_01
Patent number
US04426524

Reaction notes

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