Phenyltrimethylammonium bromide dibromide → 2-Bromo-1-((1as,5ar)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-ethanone

HRID 2261426Notes

Reaction equation

HRID 2261426 reaction equation
[CH3:1][C:2]1([CH3:15])[C@@H:4]2[CH2:5][C:6]3[C:10]([C@H:3]12)=[C:9]([CH3:11])[S:8][C:7]=3[C:12](=[O:14])[CH3:13].[Br-:16].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>C(Cl)Cl.CO.C([O-])(O)=O.[Na+].O>[Br:16][CH2:13][C:12]([C:7]1[S:8][C:9]([CH3:11])=[C:10]2[C:6]=1[CH2:5][C@H:4]1[C:2]([CH3:15])([CH3:1])[C@H:3]12)=[O:14]

Participants

7

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromide2×HCID 59380608(1aS,5aR)-1-(1,1,2-Trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-ethanone

Product 1

HCID 593806072-Bromo-1-((1as,5ar)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-ethanoneYield 66.8%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (1aS,5aR)-1-(1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-ethanone (275 mg, 1.25 mmol) in DCM (7 mL) and methanol (3.5 mL) is added phenyltrimethyl-ammoniumbromid-dibromid (570 mg, 1.5 mmol) and the reaction mixture is stirred at rt for 30 min. Another portion of phenyltrimethyl-ammoniumbromid-dibromid (600 mg, 1.6 mmol) is added and stirring is continued for 1 h before the mixture is diluted with sat. aq. NaHCO3 (5 mL) and water (25 mL) and extracted twice with DCM (2×20 mL). The organic extracts are dried over Na2SO4 and evaporated to give crude 2-bromo-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-ethanone (250 mg) as a brownish oil; LC-MS: tR=1.06 min, [M+3]+=300.99.

Workup

  1. stirringstirring
  2. waitis continued for 1 h before the mixture
  3. extractionextracted twice with DCM (2×20 mL)
  4. dry with materialThe organic extracts are dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-9ec6d19e99c94eda8cab500d1ed19dc0
Source dataset
uspto-grants-2010_12
Patent number
US07846964B2

Reaction notes

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