1-(2,4-Bis(benzyloxy)-5-chlorophenyl)ethanone → 1-(2,4-Bis-benzyloxy-5-chloro-phenyl)-2-bromo-ethanone

HRID 1433138Notes

Reaction equation

HRID 1433138 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)[C:45]([Cl:56])=[CH:44][C:43]=1[C:57](=[O:59])[CH3:58])[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:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:45]([Cl:56])=[CH:44][C:43]=1[C:57](=[O:59])[CH2:58][Br:1])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 179636911-(2,4-Bis(benzyloxy)-5-chlorophenyl)ethanoneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 579348271-(2,4-Bis-benzyloxy-5-chloro-phenyl)-2-bromo-ethanoneYield 53.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyltrimethylammonium tribromide (7.5 g, 0.02 mol) was added portionwise to a stirred solution of 1-(2,4-Bis-benzyloxy-5-chloro-phenyl)-ethanone (7.09 g, 0.019 mol) in tetrahydrofuran (100 ml) and the mixture was stirred for 2 h. The mixture was partitioned between water (100 ml) and diethyl ether (2×50 ml). The combined organic phases were dried over magnesium sulphate and concentrated to give a beige solid. Crystallisation from toluene (100 ml) gave 1-(2,4-Bis-benzyloxy-5-chloro-phenyl)-2-bromo-ethanone as a white solid (4.5 g)

Workup

  1. customThe mixture was partitioned between water (100 ml) and diethyl ether (2×50 ml)
  2. dry with materialThe combined organic phases were dried over magnesium sulphate
  3. concentrationconcentrated
  4. customto give a beige solid
  5. customCrystallisation from toluene (100 ml)

Sources & evidence

ORD record
ord-24cb3e52125b4536bf0112c2a64839ed
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Reaction notes

Loading…