N-bromobutanimide → HCID 12026771, compound

HRID 1897563Notes

Reaction equation

HRID 1897563 reaction equation
[C:1]([C:5]1[O:9][C:8]([CH3:10])=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[C:1]([C:5]1[O:9][C:8]([CH2:10][Br:15])=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 68410379HCID 68410379, compound

Product 1

HCID 12026771HCID 12026771, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of methyl 5-tert-butyl-2-methylfuran-3-carboxylate (10.4 g, 53 mmol), N-bromosuccinimide(9.9 g, 55 mmol), and azobisisobutyronitrile (0.1 g, 0.6 mmol) in carbon tetrachloride (100 mL) was heated to reflux for 1.5 h. The suspension was cooled to room temperature, and succinimide was removed by filtration and rinsed with carbon tetrachloride. The combined filtrates were evaporated to dryness. The residue was subjected to Kugelrohr distillation (<1 mbar, 110-120° C.) to yield methyl 5-tert-butyl-2-(bromomethyl)furan-3-carboxylate (14.3 g, 98% yield) as a light-yellow oil. 1H-NMR (300 MHz, CDCl3): δ 6.28 (s, 1H), 4.80 (s, 2H), 3.85 (s, 3H), 1.28 (s, 9H) ppm.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 h
  3. customsuccinimide was removed by filtration
  4. washrinsed with carbon tetrachloride
  5. customThe combined filtrates were evaporated to dryness
  6. distillationThe residue was subjected to Kugelrohr distillation (<1 mbar, 110-120° C.)

Sources & evidence

ORD record
ord-0d0ce0f2fb91453ca230d66c65053c89
Source dataset
uspto-grants-2013_08
Patent number
US08519137B2

Reaction notes

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