1,1,1,3-Tetrabromopropan-2-one → 2,4-Dibromo-6-cyclopropyl-8-(4-(trifluoromethyl)phenylsulfonyl)-8-azabicyclo[3.2.1]oct-6-en-3-one

HRID 2061624Notes

Reaction equation

HRID 2061624 reaction equation
C([Zn]CC)C.[CH:6]1([C:9]2[CH:13]=[CH:12][N:11]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:10]=2)[CH2:8][CH2:7]1.[Br:27][CH2:28][C:29]([C:31](Br)(Br)[Br:32])=[O:30]>CCCCCC.C1(C)C=CC=CC=1.CCOC(C)=O>[Br:27][CH:28]1[C:29](=[O:30])[CH:31]([Br:32])[CH:10]2[N:11]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:25])([F:26])[F:24])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:12]1[CH:13]=[C:9]2[CH:6]1[CH2:7][CH2:8]1

Participants

7

Reactant 3

HCID 544451991,1,1,3-Tetrabromopropan-2-oneHCID 67309479HCID 67309479, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 673034852,4-Dibromo-6-cyclopropyl-8-(4-(trifluoromethyl)phenylsulfonyl)-8-azabicyclo[3.2.1]oct-6-en-3-oneYield 62%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diethyl zinc (18.1 mL, 18.1 mmol of a 1M solution in hexane) was added to a solution of 3-cyclopropyl-1-(4-(trifluoromethyl)phenylsulfonyl)-1H-pyrrole (3.18 g, 10.1 mmol) and tetrabromoacetone (7.53 g, 20.1 mmol) in toluene at −10° C. The reaction mixture was stirred at room temperature for 17 h and was subsequently diluted with EtOAc and washed with saturated aqueous Na2CO3. The organic phase was separated, dried (Na2SO4), filtered, concentrated under vacuum and purified on a silica gel column (eluant hexane/EtOAc, 9/1 to 7/3, v/v) to give compound 115 (3.31 g, 6.25 mmol, 62%). MS (ESI) 530.0 (M+H).

Workup

  1. washwashed with saturated aqueous Na2CO3
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. custompurified on a silica gel column (eluant hexane/EtOAc, 9/1 to 7/3

Sources & evidence

ORD record
ord-63280baf3a0b430bb6d6b658f53758c8
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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