Allyl bromide → HCID 67540875, compound

HRID 579680Notes

Reaction equation

HRID 579680 reaction equation
[OH-].[Na+].[CH3:3][CH:4]([CH3:49])[CH2:5][N:6]1[C:18]2[CH:17]=[CH:16][C:15]([C:19]3[CH:20]=[CH:21][C:22]4[NH:23][C:24]5[C:29]([C:30]=4[CH:31]=3)=[CH:28][C:27]([C:32]3[CH:33]=[CH:34][C:35]4[N:36]([CH2:45][CH:46]([CH3:48])[CH3:47])[C:37]6[C:42]([C:43]=4[CH:44]=3)=[CH:41][CH:40]=[CH:39][CH:38]=6)=[CH:26][CH:25]=5)=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2.[CH2:50](Br)[CH:51]=[CH2:52]>CS(C)=O>[CH3:3][CH:4]([CH3:49])[CH2:5][N:6]1[C:18]2[CH:17]=[CH:16][C:15]([C:19]3[CH:20]=[CH:21][C:22]4[N:23]([CH2:52][CH:51]=[CH2:50])[C:24]5[C:29]([C:30]=4[CH:31]=3)=[CH:28][C:27]([C:32]3[CH:33]=[CH:34][C:35]4[N:36]([CH2:45][CH:46]([CH3:48])[CH3:47])[C:37]6[C:42]([C:43]=4[CH:44]=3)=[CH:41][CH:40]=[CH:39][CH:38]=6)=[CH:26][CH:25]=5)=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 67540920HCID 67540920, compound

Product 1

HCID 67540875HCID 67540875, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of NaOH (0.1 g, 2.58 mmol) and 7 (0.26 g, 0.43 mmol) in DMSO (20 ml) was stirred at room temperature for 10 minutes before allylbromide (0.26 g, 2.13 mmol) was added in one portion. The mixture was stirred for another 3 hours before quenching with water followed by extraction with methylene chloride. The organic extracts were combined, washed with water and dried over MgSO4. Upon evaporating off the solvent, the crude product was purified by column chromatography on silica gel using hexane/methylene chloride 4:1 (v/v) as the eluent to yield 8 (0.14 g, 49%) as a white powder. 1H NMR (400 MHz, CDCl3, 298 K): δ(ppm) 8.52-8.44 (m, 4H), 8.21-8.19 (d, 2H), 7.87-7.84 (m, 4H), 7.52-7.42 (m, 8H), 7.27-7.25 (m, 2H), 6.15-6.02 (m, 1H), 5.28-5.12 (m, 2H), 5.02-5.01 (d, 2H), 4.16-4.14 (d, 4H), 2.50-2.40 (m, 2H), 1.04-1.03 (d, 12H).

Workup

  1. additionwas added in one portion
  2. custombefore quenching with water
  3. extractionfollowed by extraction with methylene chloride
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. customUpon evaporating off the solvent
  7. customthe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c0171474d9ba4dd4a8a013c53605976e
Source dataset
uspto-grants-2015_05
Patent number
US09040718B2

Reaction notes

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