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

HRID 2188797Notes

Reaction equation

HRID 2188797 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>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

4

Reactant 2

HCID 112657201-(3-Nitro-4-phenylmethoxyphenyl)ethanoneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 110894102-Bromo-1-(3-nitro-4-phenylmethoxyphenyl)ethanoneYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyltrimethylammonium tribromide (109.00 g, 290.00 mmol) was added to a solution of 1-(4-benzyloxy-3-nitrophenyl)ethanone (2) (65.60 g, 242.00 mmol) in anhydrous THF (600 mL) in three portions, and the reaction mixture was stirred at rt for 12 h. The solids were then collected by filtration and the filtrate concentrated. The product was precipitated from chloroform upon the addition of hexanes, then collected by filtration and dried under vacuum to give bromo ketone 3 as a light yellow solid (63.33 g, 75% yield): 1H NMR (500 MHz, CDCl3) δ 4.37 (s, 3H), 5.35 (s, 2H), 7.21 (d, 1H), 7.40 (m, 5H), 8.15 (dd, 1H), 8.49 (d, 1H).

Workup

  1. filtrationThe solids were then collected by filtration
  2. concentrationthe filtrate concentrated
  3. customThe product was precipitated from chloroform upon the addition of hexanes
  4. filtrationcollected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-71d86d2209b842169a116828b0e69f37
Source dataset
uspto-grants-2012_12
Patent number
US08324218B2

Reaction notes

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