N-Fluorobenzenesulfonimide → HCID 68942586, compound

HRID 2218778Notes

Reaction equation

HRID 2218778 reaction equation
Br[CH:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][O:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2.C([Li])(CC)C.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:33])(=O)=O)=CC=1>C1COCC1>[F:33][CH:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][O:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2

Participants

5

Reactant 3

HCID 588007N-FluorobenzenesulfonimideHCID 6927318911-(Bromomethylene)-6,11-dihydrodibenz[b,e]oxepinHCID 178418400CID 53628100

Product 1

HCID 68942586HCID 68942586, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 11-Bromomethylene-6,11-dihydro-dibenzo[b,e]oxepine (1 eq.) in dry THF (0.1 M). Cool the solution to −78 C in a dry ice/acetone bath. Slowly add s-butyl lithium (1.2 eq., 1.3 M in cyclohexane) to the above solution. Stir the dark brown solution at −78 C. for two hours. Add a solution of N-fluorobenzene sulfonimide (1.2 eq.) in dry THF (0.4 M) over 2 minutes. Remove the cold bath and allow the reaction mixture to warm to ambient temperature. Stir the reaction mixture at room temperature for 1 hour. Quench the reaction with water. Wash the resulting mixture with saturated aqueous NaHCO3.

Workup

  1. temperatureCool the solution to −78 C in a dry ice/acetone bath
  2. customRemove the cold bath
  3. stirringStir the reaction mixture at room temperature for 1 hour
  4. customQuench
  5. customthe reaction with water
  6. washWash the resulting mixture with saturated aqueous NaHCO3

Sources & evidence

ORD record
ord-0bb26cd8a06a49529a2930f4cd921e2c
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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