3-Phenoxybenzyl alcohol → (2-Bromo-5-phenoxyphenyl)methanol

HRID 897511

Reaction equation

HRID 897511 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][OH:15])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O>C(#N)C>[Br:16][C:11]1[CH:12]=[CH:13][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:9][C:10]=1[CH2:14][OH:15]

Participants

4

Reactant 2

HCID 262953-Phenoxybenzyl alcoholHCID 67184N-bromobutanimide

Product 1

HCID 22346758(2-Bromo-5-phenoxyphenyl)methanolYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-phenoxyphenyl methanol (4.0 g, 0.020 mol) in anhydrous acetonitrile was added 1-bromo-2,5-pyrrolidinedione (3.73 g, 0.021 mol) at room temperature. The mixture was stirred at room temperature for one and a half hour under an atmosphere of nitrogen. The solvents were removed under the reduced pressure. Tetrachloromethane (100 mL) was added to the residue, and the mixture was filtered. The filtrate was concentrated into the residue, and the residue was purified by flash chromatography on silica gel using ethyl acetate/n-heptane (1:5) as mobile phase to yield (2-bromo-5-phenoxyphenyl)methanol (4.7 g, 0.017 mol):

Workup

  1. customThe solvents were removed under the reduced pressure
  2. additionTetrachloromethane (100 mL) was added to the residue
  3. filtrationthe mixture was filtered
  4. concentrationThe filtrate was concentrated into the residue
  5. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-4c6e8c4653174f90ad0e7c0236601317
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Linked notes

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