Phenyltrimethylammonium bromide dibromide → HCID 58045888, compound

HRID 657950Notes

Reaction equation

HRID 657950 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:18](=[O:20])[CH3:19])[CH:8]=[C:9]([O:11][CH2:12][CH2:13][C:14]([F:17])([F:16])[F:15])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Br-:21].[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>C1COCC1.CO.C(OCC)(=O)C>[Br:21][CH2:19][C:18]([C:7]1[CH:8]=[C:9]([O:11][CH2:12][CH2:13][C:14]([F:17])([F:16])[F:15])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1)=[O:20]

Participants

6

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 58045746HCID 58045746, compound

Product 1

HCID 58045888HCID 58045888, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-[3-tert-Butyl-5-(3,3,3-trifluoropropoxy)phenyl]ethanone (O2.107; 170 mg, 0.59 mmol) was dissolved in a mixture of THF (3 ml) and methanol (3 ml). While stirring, phenyltrimethylammonium tribromide (222 mg, 0.59 mmol) was introduced and the mixture was stirred overnight. The reaction mixture was diluted with ethyl acetate and washed with saturated sodium hydrogencarbonate solution. After drying over sodium sulfate, the solvent was removed and the residue was purified by flash chromatography (n-heptane:ethyl acetate). Yield: 42 mg,

Workup

  1. stirringthe mixture was stirred overnight
  2. washwashed with saturated sodium hydrogencarbonate solution
  3. dry with materialAfter drying over sodium sulfate
  4. customthe solvent was removed
  5. customthe residue was purified by flash chromatography (n-heptane:ethyl acetate)

Sources & evidence

ORD record
ord-eb4ffc3e4b5d4472b7ac9d2a0f57ef11
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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