Bromine → HCID 68743707, compound

HRID 2378542Notes

Reaction equation

HRID 2378542 reaction equation
[CH:1]1([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.BrBr.C1C(=O)N([Br:30])C(=O)C1>C(#N)C>[Br:30][C:13]1[C:8]([O:7][CH2:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[N:9][CH:10]=[C:11]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:12]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 67184N-bromobutanimideHCID 68743754HCID 68743754, compound

Product 1

HCID 68743707HCID 68743707, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of Intermediate 31 (5.20 g) in acetonitrile (50 ml) was warmed to 35° C., added dropwise with bromine (1.1 ml, WAKO), then added with NBS (3.72 g), and stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, then added with ethyl acetate (200 ml), and washed successively with saturated aqueous ammonium chloride, 5% aqueous sodium sulfite, saturated aqueous sodium hydrogencarbonate and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=10:1) to obtain the title compound (Compound No. E-1, 6.51 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionadded with ethyl acetate (200 ml)
  3. washwashed successively with saturated aqueous ammonium chloride, 5% aqueous sodium sulfite, saturated aqueous sodium hydrogencarbonate and saturated brine
  4. customThe organic layer was dried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography (Quad, hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-2d4e6ba7d9d242e6bebd7806ef775a33
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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