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

HRID 2075925Notes

Reaction equation

HRID 2075925 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 2M 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 2M aqu
  4. dry with materialNaOH, water and brine and dry it with Na2SO4

Sources & evidence

ORD record
ord-aee0be06c736410ea67cd9e3d61de5c7
Source dataset
uspto-grants-2011_04
Patent number
US07923473B2

Reaction notes

Loading…