Sodium Thiosulfate → 2-Bromo-1-(3-nitro-4-phenylmethoxyphenyl)ethanone

HRID 1696823Notes

Reaction equation

HRID 1696823 reaction equation
[Br-:1].[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.[CH2:34]([O:41][C:42]1[CH:47]=[CH:46][C:45]([C:48](=[O:50])[CH3:49])=[CH:44][C:43]=1[N+:51]([O-:53])=[O:52])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1>[CH2:34]([O:41][C:42]1[CH:47]=[CH:46][C:45]([C:48](=[O:50])[CH2:49][Br:1])=[CH:44][C:43]=1[N+:51]([O-:53])=[O:52])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 112657201-(3-Nitro-4-phenylmethoxyphenyl)ethanoneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 110894102-Bromo-1-(3-nitro-4-phenylmethoxyphenyl)ethanoneYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyltrimethylammonium tribromide (1.46 g, 3.90 mmol) was added to a solution of 1-(4-benzyloxy-3-nitrophenyl)ethanone (2) (1.04 g, 3.82 mmol) in anhydrous THF (15 mL) in three portions. The reaction mixture was stirred at rt for 12 h. Then an aqueous sodium bicarbonate solution (5%, 10 mL) and an aqueous sodium thiosulfate solution (10%, 5 mL) were added. The mixture was extracted with dichloromethane, and combined organics were concentrated by rotary evaporation. The resulting residue was purified by Biotage silica gel column chromatography eluting with dichloromethane to give bromo ketone 3 as a white solid (1.08 g, 81% yield): 1H NMR (500 MHz, CDCl3) δ 4.49 (s, 3H), 5.35 (s, 2H), 7.21 (d, 1H), 7.40 (m, 5H), 8.15 (dd, 1H), 8.49 (d, 1H).

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. concentrationcombined organics were concentrated by rotary evaporation
  3. customThe resulting residue was purified by Biotage silica gel column chromatography
  4. washeluting with dichloromethane

Sources & evidence

ORD record
ord-0e144f60fcda4904aea0c13452bf9bed
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

Loading…