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

HRID 2060348Notes

Reaction equation

HRID 2060348 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 78.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

DK001 (The following reaction is carried out under exclusion of light.) Dissolve 2-Methyl-furan-3-carboxylic acid methyl ester (52) (3.60 mL, 28.5 mmol) in chloroform (20 mL) and glacial acetic acid (20 mL) and add NBS (6.90 g, 38.8 mmol) portionwise in between a period of 95 min. Stir the reaction suspension for additional 19 h at rt. Add water to the reaction mixture and extract the aqu. layer with dichloromethane (2 times), wash the combined organic layer with 2M aqu. NaOH, water (3 times) and brine and dry it with Na2SO4 to obtain 5-Bromo-2-methyl-furan-3-carboxylic acid methyl ester (53) (4.90 g, 78%) 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. customDK001 (The following reaction
  2. extractionAdd water to the reaction mixture and extract the aqu
  3. washlayer with dichloromethane (2 times), wash the combined organic layer with 2M aqu
  4. dry with materialNaOH, water (3 times) and brine and dry it with Na2SO4

Sources & evidence

ORD record
ord-ae48d01c89fe4266930b7956b2d33554
Source dataset
uspto-grants-2012_10
Patent number
US08278356B2

Reaction notes

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