Phenyltrimethylammonium bromide dibromide → 2-Bromo-1-[3-tert-butyl-5-(3-hydroxypropoxy)-4-methoxyphenyl]ethanone

HRID 657944Notes

Reaction equation

HRID 657944 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:24](=[O:26])[CH3:25])[CH:8]=[C:9]([O:13][CH2:14][CH2:15][CH2:16][O:17]C2CCCCO2)[C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[Br-:27].[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.C(Cl)Cl>[Br:27][CH2:25][C:24]([C:7]1[CH:8]=[C:9]([O:13][CH2:14][CH2:15][CH2:16][OH:17])[C:10]([O:11][CH3:12])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=1)=[O:26]

Participants

5

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 581367841-{3-tert-Butyl-4-methoxy-5-[3-(tetrahydropyran-2-yloxy)propoxy]phenyl}ethanone

Product 1

HCID 581369012-Bromo-1-[3-tert-butyl-5-(3-hydroxypropoxy)-4-methoxyphenyl]ethanoneYield 45.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1-{3-tert-Butyl-4-methoxy-5-[3-(tetrahydropyran-2-yloxy)propoxy]phenyl}ethanone (2.071; 12.7 g) was dissolved in methanol/THF (200/200 ml) and admixed with phenyltrimethylammonium tribromide (13.1 g) while stirring. The mixture was stirred at RT for 1 h, then diluted with DCM and washed once with 5% sodium thiosulfate solution. The DCM phase was dried over magnesium sulfate, filtered and concentrated. The residue was taken up in acetonitrile (100 ml) and admixed with 48% hydrobromic acid (5.91 ml). The mixture was left to stand for 1 h, then admixed with water, extracted by shaking with EA, and the combined EA phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified using silica gel (120 g cartridge, n-heptane/MtB ether gradient of 0-100% in 60 min). 3.29 g of the title compound were obtained.

Workup

  1. stirringThe mixture was stirred at RT for 1 h
  2. washwashed once with 5% sodium thiosulfate solution
  3. dry with materialThe DCM phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. waitThe mixture was left
  7. extractionextracted
  8. stirringby shaking with EA
  9. dry with materialthe combined EA phases were dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified
  13. customsilica gel (120 g cartridge, n-heptane/MtB ether gradient of 0-100% in 60 min)

Sources & evidence

ORD record
ord-f42e0527f7ba4798b96bf5820256b411
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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