Methanol → Methyl 5-bromofuran-2-carboxylate

HRID 1938146Notes

Reaction equation

HRID 1938146 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[CH:10]1N=CN(C(N2C=NC=C2)=O)C=1.CO>C(Cl)Cl.CCCCC>[Br:1][C:2]1[O:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 682631,1'-CarbonyldiimidazoleHCID 685115-Bromo-2-furanecarboxylic acid

Product 1

HCID 599633Methyl 5-bromofuran-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8003PentaneSolvent

Procedure

To a slurry of 15.00 g (0.0785 mol) of 5-bromofuranoic acid in 500 ml of methylene chloride, was added 12.73 g (0.0785 mol) of N,N-carbonyldiimidazole. After reacting at room temperature overnight, 6.4 ml (0.157 mol) of methanol was added and the resultant mixture was stirred for approximately one hour and then washed sequentially with a 0.5M sodium hydroxide solution (twice) and a 1M hydrochloric acid solution. The organic portion was dried over sodium sulfate, filtered and then concentrated in vacuo to provide a residue. This residue was slurried in pentane to provide a white solid.

Workup

  1. washwashed sequentially with a 0.5M sodium hydroxide solution (twice) and a 1M hydrochloric acid solution
  2. dry with materialThe organic portion was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide a residue
  6. customto provide a white solid

Sources & evidence

ORD record
ord-ce7a2eb5f8b548cca03b1f3aa5231643
Source dataset
uspto-grants-1997_12
Patent number
US05693611

Reaction notes

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