N-bromobutanimide → (2-Bromo-5-methoxyphenyl)methanol

HRID 1372175Notes

Reaction equation

HRID 1372175 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][OH:7].C1C(=O)N([Br:18])C(=O)C1>C(#N)C>[Br:18][C:8]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH2:6][OH:7]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 814373-Methoxybenzyl alcohol

Product 1

HCID 10867706(2-Bromo-5-methoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared by reacting 3-methoxybenzyl alcohol (13.82 g, 0.1 mol) and NBS (19.58 g, 0.11 mol) in acetonitrile (250 mL) at room temperature for 3 hr. The solvent was removed and the resulting mass slurried in dichloromethane (250 mL) and filtered to remove the insoluble succinimide side product. The crude material was purified by chromatography (20% EtOAc-hexanes) to provide a white solid (17.69 g, 81%), mp 57–58° C.

Workup

  1. customat room temperature
  2. customfor 3 hr
  3. customThe solvent was removed
  4. filtrationfiltered
  5. customto remove the insoluble succinimide side product
  6. customThe crude material was purified by chromatography (20% EtOAc-hexanes)

Sources & evidence

ORD record
ord-2e567bcf26cd4ebe906c34f246d516d5
Source dataset
uspto-grants-2007_01
Patent number
US07157492B2

Reaction notes

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