N-bromobutanimide → Methyl 5-bromo-2-methylfuran-3-carboxylate

HRID 1944254Notes

Reaction equation

HRID 1944254 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[CH:8][O:7][C:6]=1[CH3:10])=[O:4].C1C(=O)N([Br:18])C(=O)C1>C(Cl)(Cl)Cl.C(O)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([Br:18])[O:7][C:6]=1[CH3:10])=[O:4]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 80237Methyl 2-methylfuran-3-carboxylate

Product 1

HCID 15534190Methyl 5-bromo-2-methylfuran-3-carboxylateYield 80.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

(The following reaction is done under exclusion of light.) Dissolve 2-Methyl-furan-3-carboxylic acid methyl ester (15) (2.00 mL, 15.9 mmol) in chloroform (11 mL) and glacial acetic acid (11 mL) and add NBS (3.85 g, 21.6 mmol) portionwise in between a period of 75 min. Stir the reaction suspension for additional 16 h at rt. Add water to the reaction mixture and extract the aqu. layer with DCM (2 times), wash the combined organic layer with 2 M aqu. NaOH, water and brine and dry it with Na2SO4 to obtain 5-Bromo-2-methyl-furan-3-carboxylic acid methyl ester (16) (2.80 g, 80%) as a red brown oil. No further purification. 1H NMR (400 MHz, CDCl3): 2.54 (s, 3H); 3.80 (s, 3H); 6.53 (s, 1H).

Workup

  1. custom(The following reaction
  2. extractionAdd water to the reaction mixture and extract the aqu
  3. washlayer with DCM (2 times), wash the combined organic layer with 2 M aqu
  4. dry with materialNaOH, water and brine and dry it with Na2SO4

Sources & evidence

ORD record
ord-f902fba2e46a4d50bdd64c87a6d6deb6
Source dataset
uspto-grants-2013_03
Patent number
US08394835B2

Reaction notes

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