Phenyltrimethylammonium bromide dibromide → HCID 58136870, compound

HRID 657934Notes

Reaction equation

HRID 657934 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:15](=[O:17])[CH3:16])[CH:8]=[C:9]([CH2:11][O:12][CH2:13][CH3:14])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Br-:18].[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>CO.C1COCC1>[Br:18][CH2:16][C:15]([C:7]1[CH:8]=[C:9]([CH2:11][O:12][CH2:13][CH3:14])[CH:10]=[C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])[CH:6]=1)=[O:17]

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 58137010HCID 58137010, compound

Product 1

HCID 58136870HCID 58136870, compoundYield 132.8%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1-(3-tert-Butyl-5-ethoxymethylphenyl)ethanone (O2.008; 550 mg) was dissolved in methanol/THF (10 ml/10 ml), admixed with phenyltrimethylammonium tribromide (882 mg) while stirring and stirred at RT for 2 h. Subsequently, the reaction mixture was poured onto DCM (200 ml) and washed thoroughly once with 5% sodium thiosulfate solution and once with water. Then the DCM phase was dried and concentrated. The residue was purified using silica gel (40 g cartridge, n-heptane/EA gradient of 0-50% in 30 min). 566 mg of the title compound were obtained. LC-MS rt: 1.83 min [M+H]+: 313.2 (met. a)

Workup

  1. stirringstirred at RT for 2 h
  2. additionSubsequently, the reaction mixture was poured onto DCM (200 ml)
  3. washwashed thoroughly once with 5% sodium thiosulfate solution and once with water
  4. dry with materialThen the DCM phase was dried
  5. concentrationconcentrated
  6. customThe residue was purified
  7. customsilica gel (40 g cartridge, n-heptane/EA gradient of 0-50% in 30 min)

Sources & evidence

ORD record
ord-1a8b86802fdc4d4e8e8b1397aa955de0
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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