m-Chloroperbenzoic acid → 3-fluoro-6,10b-dihydro-1aH-dibenzo-[3,4:6,7]cyclohept[1,2-b]oxirene

HRID 47222Notes

Reaction equation

HRID 47222 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([O:10]O)=O)[CH:3]=1.[F:12][C:13]1[CH:27]=[CH:26][C:16]2[CH2:17]C3C=CC=CC=3C=[CH:21][C:15]=2[CH:14]=1>C(Cl)(Cl)Cl.C1(O)C=CC(O)=CC=1>[F:12][C:13]1[CH:27]=[CH:26][C:16]2[CH2:17][C:5]3[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=3[CH:8]3[O:10][CH:21]3[C:15]=2[CH:14]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 227441622-fluoro-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 865887003-fluoro-6,10b-dihydro-1aH-dibenzo-[3,4:6,7]cyclohept[1,2-b]oxireneYield 110.4%

Reagents, catalysts & solvents 2

HCID 785HydroquinoneCatalystHCID 6212ChloroformSolvent2×

Conditions

Temperature
60 °C

Procedure

Metachloroperbenzoic acid (0.0501 mol) was dissolved in CHCl3 (40 ml). The organic solution was dried, filtered and the filtrate was added dropwise to a solution of intermediate 1 (0.0417 mol) and 1,4-benzenediol (0.26 g) in CHCl3 (70 ml), stirred at 60° C. The reaction mixture was stirred for 2.5 hours at 60° C., then cooled on an ice-bath, washed with a 10% aqueous Na2CO3 solution and brine, dried, filtered and the filtrate was evaporated, yielding 10.42 g of 3-fluoro-6,10b-dihydro-1aH-dibenzo-[3,4:6,7]cyclohept[1,2-b]oxirene (intermediate 2)

Workup

  1. customThe organic solution was dried
  2. filtrationfiltered
  3. stirringThe reaction mixture was stirred for 2.5 hours at 60° C.
  4. temperaturecooled on an ice-bath
  5. washwashed with a 10% aqueous Na2CO3 solution and brine
  6. customdried
  7. filtrationfiltered
  8. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-424a33c7ff4a4967b15f279e092981f9
Source dataset
uspto-grants-2004_03
Patent number
US06699858B2

Reaction notes

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