1-(2,4-Bis(benzyloxy)phenyl)ethanone → 1-(2,4-Bis-benzyloxyphenyl)-2-bromo-ethanone

HRID 1433166Notes

Reaction equation

HRID 1433166 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]=[C:46]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:45]=[CH:44][C:43]=1[C:56](=[O:58])[CH3:57])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>O1CCCC1>[CH2:34]([O:41][C:42]1[CH:47]=[C:46]([O:48][CH2:49][C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[CH:45]=[CH:44][C:43]=1[C:56](=[O:58])[CH2:57][Br:1])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

4

Reactant 2

HCID 3194691-(2,4-Bis(benzyloxy)phenyl)ethanoneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 579348191-(2,4-Bis-benzyloxyphenyl)-2-bromo-ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyltrimethylammonium tribromide (5.6 g, 0.015 mol) was added portionwise to a stirred solution of 1-(2,4-Bis-benzyloxyphenyl)-ethanone (5.0 g, 0.015 mol) in tetrahydrofuran (50 ml) and the mixture was stirred for 2 h. The mixture was partitioned between water (50 ml) and diethyl ether (2×50 ml). The combined organic phases were dried over magnesium sulphate and concentrated to give 1-(2,4-Bis-benzyloxyphenyl)-2-bromo-ethanone as a beige solid which was used without further purification.

Workup

  1. customThe mixture was partitioned between water (50 ml) and diethyl ether (2×50 ml)
  2. dry with materialThe combined organic phases were dried over magnesium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-41257940547c4bf893d8098d874e9bea
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Reaction notes

Loading…