N-bromobutanimide → 3-Acetyl-6-(bromomethyl)-4-hydroxy-2H-pyran-2-one

HRID 1757041Notes

Reaction equation

HRID 1757041 reaction equation
[C:1]([C:4]1[C:5](=[O:12])[O:6][C:7]([CH3:11])=[CH:8][C:9]=1[OH:10])(=[O:3])[CH3:2].[Br:13]N1C(=O)CCC1=O>ClCCl>[C:1]([C:4]1[C:5](=[O:12])[O:6][C:7]([CH2:11][Br:13])=[CH:8][C:9]=1[OH:10])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 546784943-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

Product 1

HCID 547239163-Acetyl-6-(bromomethyl)-4-hydroxy-2H-pyran-2-oneYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-acetyl-4-hydroxy-6-methylpyran-2-one (52 parts), N-bromosuccinimide (54 parts) and dichloromethane (1060 parts) were stirred at 20°-25° C. for about 4-5 hours under exposure to UV light. The dichloromethane solution was washed with water (2×500 cm3) to remove the succinimide, dried over magnesium sulphate, filtered and the solvent removed at 40° C./20 mm to leave 3-acetyl-6-bromomethyl-4-hydroxypyran-2-one (70 parts, 47%).

Workup

  1. washThe dichloromethane solution was washed with water (2×500 cm3)
  2. customto remove the succinimide
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent removed at 40° C./20 mm

Sources & evidence

ORD record
ord-7940590eee534e9bb31d2a8fb743e35c
Source dataset
uspto-grants-1995_08
Patent number
US05443970

Reaction notes

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