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Phenyltrimethylammonium bromide dibromide → 2-Bromo-1-[4-(pentafluoro-lambda6-sulfanyl)phenyl]ethanone

HRID 1523308
Notes
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Reaction equation

HRID 1523308 reaction equation
[F:1][S:2]([F:15])([F:14])([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1.[Br-:16].[Br-].[Br-].C[N+](C)(C)C1C=CC=CC=1.C[N+](C1C=CC=CC=1)(C)C.C[N+](C1C=CC=CC=1)(C)C>C1COCC1>[Br:16][CH2:10][C:9]([C:6]1[CH:5]=[CH:4][C:3]([S:2]([F:12])([F:13])([F:14])([F:15])[F:1])=[CH:8][CH:7]=1)=[O:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 597155361-[4-(Pentafluoro-lambda6-sulfanyl)phenyl]ethan-1-one

Product 1

HCID 1176012422-Bromo-1-[4-(pentafluoro-lambda6-sulfanyl)phenyl]ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-[4-(pentafluoro-λ6-sulfanyl)phenyl]ethanone (Preparation 41, 0.6 g, 2.44 mmol) in THF (20 mL) at 0° C. was added trimethylphenylammonium tribromide (0.962 g, 2.56 mmol). After stirring for 2 hours at 0° C. the reaction was quenched with a saturated aqueous solution of sodium hydrogen carbonate. The reaction was extracted with ethyl acetate and dried over MgSO4 before concentrating in vacuo to afford the title compound that was used without further purification.

Workup

  1. customwas quenched with a saturated aqueous solution of sodium hydrogen carbonate
  2. extractionThe reaction was extracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationbefore concentrating in vacuo

Sources & evidence

ORD record
ord-521fbeb30fb5407586e28e235ed7b868
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09079878B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes