Bromine → Methyl 5-bromo-3-methyl-2-furoate

HRID 1799798Notes

Reaction equation

HRID 1799798 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].[Br:11]Br>C(OCC)C>[Br:11][C:5]1[O:4][C:3]([C:7]([O:9][CH3:10])=[O:8])=[C:2]([CH3:1])[CH:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 350231Methyl 3-methyl-2-furoate

Product 1

HCID 604543Methyl 5-bromo-3-methyl-2-furoateYield 85.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of methyl 3-methylfuran-2-carboxylate (3.0 g, 21.41 mmol) in ethyl ether (100 mL) was added bromine (1.210 mL, 23.55 mmol) dropwise at RT and the mixture was allowed to stir for 14 h. Evaporation followed by purification by flash chromatography (silica gel, 0% to 10% ethyl acetate in hexanes) yielded the title compound (4.0 g, 85% yield) as a white solid: 1H NMR (500 MHz, CDCl3) δ 6.31 (s, 1H), 3.88 (s, 3H), 2.33 (s, 3H); HPLC retention time: 2.776 min, LCMS (ES): m/z 219, 221 [M+H]+.

Workup

  1. customEvaporation
  2. customfollowed by purification by flash chromatography (silica gel, 0% to 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d68a1f2ee19748ff8009e38da8bca23f
Source dataset
uspto-grants-2013_01
Patent number
US08344160B2

Reaction notes

Loading…