Phenyltrimethylammonium bromide dibromide → HCID 21255616, compound

HRID 1186043Notes

Reaction equation

HRID 1186043 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](C(=O)C)=[CH:7][C:6]=1[OH:14])([CH3:4])([CH3:3])[CH3:2].[Br-:15].[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.[O:48]1CC[CH2:50][CH2:49]1.CO>>[Br:15][CH2:50][C:49]([C:9]1[CH:8]=[CH:7][C:6]([OH:14])=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:10]=1)=[O:48]

Participants

4

Reactant 3

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 21899815MeOH tetrahydrofuranHCID 86652996HCID 86652996, compound

Product 1

HCID 21255616HCID 21255616, compound

Procedure

A solution of 1-(4-tert-Butyl-3-hydroxy-phenyl)-ethanone (192 mg, 1.0 mmol) and trimethyl-phenyl-ammonium tribromide in (3:1) tetrahydrofuran/methanol (3 mL) was stirred at room temperature 1 h. The resulting mixture was quenched with 5% wt. aq. sodium thiosulfate (500 μL) then water (3.5 mL). DCM added and the organic layer separated, dried over sodium sulfate, filtered and evaporated in vacuo to yield an amber syrup. The syrup was purified via silica gel chromatography eluting with (3:1) EtOAc/heptanes to yield 2-bromo-1-(3-tert-butyl-4-hydroxy-phenyl)-ethanone as a white solid. C12H15BrO2; MS (ESI) m/z 271/273 (MH)+.

Workup

  1. customThe resulting mixture was quenched with 5% wt. aq. sodium thiosulfate (500 μL)
  2. additionDCM added
  3. customthe organic layer separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto yield an amber syrup
  8. customThe syrup was purified via silica gel chromatography
  9. washeluting with (3:1) EtOAc/heptanes

Sources & evidence

ORD record
ord-d7f26aba3194470a9ca3e6fc83d55c95
Source dataset
uspto-grants-2014_03
Patent number
US08673890B2

Reaction notes

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