N-bromobutanimide → Tert-butyl 2-bromo-4,5,7,8-tetrahydrofuro[3,2-c]azepine-6-carboxylate

HRID 1518544Notes

Reaction equation

HRID 1518544 reaction equation
[O:1]1[C:10]2[CH2:9][CH2:8][CH:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[NH:6][CH2:5][C:4]=2[CH:3]=[CH:2]1.[Br:18]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C>[Br:18][C:2]1[O:1][C:10]2[CH2:9][CH2:8][CH:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[NH:6][CH2:5][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 67269469HCID 67269469, compound

Product 1

HCID 67269056Tert-butyl 2-bromo-4,5,7,8-tetrahydrofuro[3,2-c]azepine-6-carboxylate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

A solution of tert-butyl 4,5,7,8-tetrahydrofuro[3,2-c]azepine-6-carboxylate (0.21 mmol) in chloroform (0.5 mL) and acetic acid (0.5 mL) is treated with N-bromosuccinimide (0.21 mmol) at RT. After 1 hour, the reaction is poured over saturated aqueous NaHCO3, and extracted with ethyl acetate (2×5 mL). The organic layers are washed with brine, dried, and purified by silica chromatography (20% ethyl acetate/hexanes) to give tert-butyl 2-bromo-4,5,7,8-tetrahydrofuro[3,2-c]azepine-6-carboxylate.

Workup

  1. extractionextracted with ethyl acetate (2×5 mL)
  2. washThe organic layers are washed with brine
  3. customdried
  4. custompurified by silica chromatography (20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-694b817e0c7a4e22b79d3be6bda31b41
Source dataset
uspto-grants-2012_07
Patent number
US08232406B2

Reaction notes

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