Benzyl Bromide → HCID 69843740, compound

HRID 2227130Notes

Reaction equation

HRID 2227130 reaction equation
[C:1]1([C:7]2[C:11]3=[N:12][C:13](=[O:16])[C:14](=[O:15])[C:10]3=[N:9][C:8]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:23]([N:12]1[C:11]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:8]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:9]([CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:10]=2[C:14](=[O:15])[C:13]1=[O:16])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 69112758HCID 69112758, compound2×

Product 1

HCID 69843740HCID 69843740, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A 100 ml round-bottom flask equipped with a stirrer and reflux condenser is charged with 1.47 g (5.1 mmol) of diphenyl-diketopyrrolopyrrole (hereinafter referred to DPP), 3.44 g (20.1 mmol) of benzyl bromide, 1.38 g (10.0 mmol) of K2CO3 and 50 ml of DMF. Under nitrogen atmosphere, the mixture is stirred and heated at 100° C. for 42.5 hours. The slurry is cooled and the orange solid is isolated by filtration. The solid is washed with water and MeOH, followed by dissolving in hot CHCl3. This CHCl3 solution is applied to silica gel column using CH2Cl2 as eluent. After condensation, 1.21 g of an orange solid is obtained (51%).

Workup

  1. customA 100 ml round-bottom flask equipped with a stirrer
  2. temperaturereflux condenser
  3. temperatureThe slurry is cooled
  4. customthe orange solid is isolated by filtration
  5. washThe solid is washed with water and MeOH
  6. dissolutionby dissolving in hot CHCl3
  7. customAfter condensation

Sources & evidence

ORD record
ord-fa3931b1f7fd4f1ea086ee8953de38b7
Source dataset
uspto-grants-2002_07
Patent number
US06413655B2

Reaction notes

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