Bromine → 3-Bromobicyclo[4.2.0]octa-1,3,5-triene

Bicyclo[4.2.0]octa-1(6),2,4-triene 5a (7.9 g, 76 mmol) was dissolved in 80 mL of water at room temperature. Upon cooling by an ice-water, 3.9 mL of bromine was added dropwise. Upon completion of the addition, the ice-water bath was removed and the reaction mixture was warmed up to room temperature and stirred overnight. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was diluted with 50 mL of n-hexane and sodium sulfite (3 g, 23.8 mmol) was added. Upon completion of the addition, the mixture was stirred at room temperature for 30 minutes. Then the separated organic layer was dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure to obtain the title compound 3-bromo-bicyclo[4.2.0]octa-1(6),2,4-triene 5b (13.53 g) as a colourless oil, which was directly used in the next step.

1. additionwas added dropwise
2. additionUpon completion of the addition
3. customthe ice-water bath was removed
4. additionwas added
5. additionUpon completion of the addition
6. stirringthe mixture was stirred at room temperature for 30 minutes
7. dry with materialThen the separated organic layer was dried over anhydrous sodium sulfate
8. filtrationfiltered
9. customto remove the drying agent
10. concentrationconcentrated under reduced pressure

ORD record

ord-73979fc817a84d85b6a6ad105883c357

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367710B2