N-bromobutanimide → HCID 59488757, compound

HRID 221942Notes

Reaction equation

HRID 221942 reaction equation
[CH:1]([O:4][C:5]([C:7]1[C:16]2[C:11](=[C:12](C(C)C)[CH:13]=[CH:14][CH:15]=2)[C:10]([C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21])=[C:9](C(C)C)[C:8]=1[Si](C)(C)C)=[O:6])([CH3:3])[CH3:2].[Br:33]N1C(=O)CCC1=O>C(#N)C>[CH:1]([O:4][C:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21])=[CH:9][C:8]=1[Br:33])=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 68506061HCID 68506061, compound

Product 1

HCID 59488757HCID 59488757, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

Under a nitrogen stream, a mixture of diisopropyl 2-trimethylsilanyl-naphthalene-1,4-dicarboxylic acid diisopropyl ester (0.25 g, 0.671 mmol), N-bromosuccinimide (179 mg, 1.006 mmol) and acetonitrile (12.5 mL) was stirred for 30 minutes at 150° C. under microwave irradiation. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel flash column chromatography (developing solution=ethyl acetate:n-hexane (1:9)), to thereby obtain the titled compound (209 mg, 82%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel flash column chromatography (developing solution=ethyl acetate:n-hexane (1:9))

Sources & evidence

ORD record
ord-b3617be1a26e428694f9810867ec3e3f
Source dataset
uspto-grants-2012_06
Patent number
US08207134B2

Reaction notes

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