Water → Methyl 5-(2-bromoacetyl)-2-(phenylmethoxy)benzoate

HRID 1696846Notes

Reaction equation

HRID 1696846 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:36][C:37](=[O:55])[C:38]1[CH:43]=[C:42]([C:44](=[O:46])[CH3:45])[CH:41]=[CH:40][C:39]=1[O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)C.O>O1CCCC1>[CH3:34][O:36][C:37](=[O:55])[C:38]1[CH:43]=[C:42]([C:44](=[O:46])[CH2:45][Br:1])[CH:41]=[CH:40][C:39]=1[O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

5

Reactant 3

HCID 962WaterHCID 108964Ethyl 5-acetyl-2-benzyloxybenzoateHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 11824614Methyl 5-(2-bromoacetyl)-2-(phenylmethoxy)benzoateYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyltrimethyl ammonium tribromide (10.60 g, 28.20 mmol) was added in 7 portions to a stirring solution of acetophenone 44 (8.00 g, 28.10 mmol) in anhydrous tetrahydrofuran (50 mL). After 18 h, the reaction mixture was poured into water (250 mL) and stirred for 1 h. The formed precipitate was collected by vacuum filtration. Re-crystallization of the collected solid from ethanol gave the α-bromide 45 (7.35 g, 72%) as a white, needle solid: 1H NMR (500 MHz, DMSO-d6) δ 3.85 (s, 3H), 4.89 (s, 1H), 5.38 (s, 2H), 7.22 (d, 1H), 7.31-7.51 (m, 6H), 8.17-8.31 (m, 2H).

Workup

  1. filtrationThe formed precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-4bc63eb1263949a1817faeaad1e7498a
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

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