Citric Acid → 2-Bromo-1-[3-tert-butyl-5-(2-methoxyethoxy)phenyl]ethanone

HRID 1524531Notes

Reaction equation

HRID 1524531 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16](=[O:18])[CH3:17])[CH:8]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Br-:19].[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(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(Cl)Cl>CO.C1COCC1>[Br:19][CH2:17][C:16]([C:7]1[CH:8]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1)=[O:18]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6344DichloromethaneHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 581368081-[3-Tert-butyl-5-(2-methoxyethoxy)phenyl]ethanone

Product 1

HCID 581367822-Bromo-1-[3-tert-butyl-5-(2-methoxyethoxy)phenyl]ethanoneYield 292.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1-[3-tert-Butyl-5-(2-methoxyethoxy)phenyl]ethanone (O2.043; 1 g) was dissolved in methanol/THF (25 ml/25 ml), admixed with phenyltrimethylammonium tribromide (882 mg) while stirring and stirred at RT overnight. Then 50 ml of 20% citric acid solution were added and the mixture was stirred for 1 h. Subsequently, DCM (200 ml) was added and the mixture was extracted three times with DCM. Then the combined DCM phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified using silica gel (40 g cartridge, n-heptane/EA gradient of 0-30% in 30 min). 1.31 g of the title compound were obtained.

Workup

  1. stirringstirred at RT overnight
  2. stirringthe mixture was stirred for 1 h
  3. extractionthe mixture was extracted three times with DCM
  4. dry with materialThen the combined DCM phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified
  8. customsilica gel (40 g cartridge, n-heptane/EA gradient of 0-30% in 30 min)

Sources & evidence

ORD record
ord-958e19da8e0040718cbd60f337e8d7f5
Source dataset
uspto-grants-2015_07
Patent number
US09079906B2

Reaction notes

Loading…