Bromine → HCID 15337967, compound

HRID 1647498Notes

Reaction equation

HRID 1647498 reaction equation
[C:1]([C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][C:7]=2[CH:8]=1)(=[O:3])[CH3:2].[Br:17]Br>CCOCC>[Br:17][CH2:2][C:1]([C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][C:7]=2[CH:8]=1)=[O:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 19925664HCID 19925664, compound

Product 1

HCID 15337967HCID 15337967, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Acetyl-5-tert-butylbenzofuran (86.5 g) was dissolved in 800 ml of ether and, with stirring at room temperature, 63.9 g of bromine was dropped thereinto. When the crystals started to be separated, the reaction mixture was cooled with ice water. After completion of the dropping, the mixture was stirred for 30 minutes, the reaction mixture was poured into ice water and, until the crystals were dissolved, ethyl acetate was added thereto. The organic layer was washed with water for three times, dried over anhydrous magnesium sulfate, concentrated in vacuo and n-hexane was added to the residue to crystallize followed by filtrating to give 100.1 g of crystals. M.p. 100°-102° C.

Workup

  1. customto be separated
  2. temperaturethe reaction mixture was cooled with ice water
  3. stirringAfter completion of the dropping, the mixture was stirred for 30 minutes
  4. additionthe reaction mixture was poured into ice water and, until the crystals
  5. dissolutionwere dissolved
  6. additionethyl acetate was added
  7. washThe organic layer was washed with water for three times
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo and n-hexane
  10. additionwas added to the residue
  11. customto crystallize
  12. filtrationby filtrating

Sources & evidence

ORD record
ord-ad92e6f39c5d4f9aa3de9f5a98f40b9f
Source dataset
uspto-grants-1995_07
Patent number
US05432195

Reaction notes

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