Ozone → HCID 53910809, compound

HRID 1824930Notes

Reaction equation

HRID 1824930 reaction equation
[CH2:1]([C:4]1[C:9]([F:10])=[C:8]([F:11])[CH:7]=[C:6]([Br:12])[C:5]=1[OH:13])[CH:2]=C.[O:14]=[O+][O-]>ClCCl.CO>[OH:13][C:5]1[C:6]([Br:12])=[CH:7][C:8]([F:11])=[C:9]([F:10])[C:4]=1[CH2:1][CH:2]=[O:14]

Participants

5

Reactant 2

HCID 24823OzoneHCID 22144872HCID 22144872, compound

Product 1

HCID 53910809HCID 53910809, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 7.8 gm (31.45 mMol) 2-allyl-3,4-difluoro-6-bromophenol in 100 mL dichloromethane and 20 mL methanol was cooled to −78° C. and was then saturated with ozone. After 20 minutes the reaction mixture was purged with nitrogen for 10 minutes and was then treated with 5 mL dimethylsulfide. The reaction mixture was allowed to warm gradually to room temperature. After 15 hours the reaction mixture was concentrated under reduced pressure to provide the title compound.

Workup

  1. customAfter 20 minutes the reaction mixture was purged with nitrogen for 10 minutes
  2. additionwas then treated with 5 mL dimethylsulfide
  3. concentrationAfter 15 hours the reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-170a77579f9d4d30ae079fdcce01f903
Source dataset
uspto-grants-2006_05
Patent number
US07045545B1

Reaction notes

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