Dimethylformamide → HCID 14415981, compound

HRID 2405450Notes

Reaction equation

HRID 2405450 reaction equation
[CH:1]1[C:6]2[C:7]3[C:16]([C:17]4[C:22]([C:5]=2[CH:4]=[CH:3][CH:2]=1)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:15][CH:14]=[C:13]1[C:8]=3[CH:9]=[CH:10][CH:11]=[CH:12]1.CN(C)C=O.[Br:28]N1C(=O)CCC1=O>O>[Br:28][C:14]1[CH:15]=[C:16]2[C:7](=[C:8]3[C:13]=1[CH:12]=[CH:11][CH:10]=[CH:9]3)[C:6]1[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=1[C:22]1[C:17]2=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 9140Benzo(g)chryseneHCID 67184N-bromobutanimide

Product 1

HCID 14415981HCID 14415981, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A flask was charged with 5.21 g of benzo[g]chrysene and 50 mL of N,N-dimethylformamide. An N,N-dimethylformamide (10 mL) solution of 4.00 g of N-bromosuccinimide was added to the mixture. The mixture was stirred at 80° C. for 8 hours. After cooling the mixture to room temperature, the reaction solution was poured into 200 mL of water. A solid that precipitated by this operation was collected by filtration, and washed with water and methanol. The resulting solid was purified by silica gel column chromatography to obtain 5.87 g of the target 10-bromobenzo[g]chrysene (yield: 88%).

Workup

  1. temperatureAfter cooling the mixture to room temperature
  2. customA solid that precipitated by this operation
  3. filtrationwas collected by filtration
  4. washwashed with water and methanol
  5. customThe resulting solid was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5ba04dfb2a624f8191e23e2ab3c2dfa5
Source dataset
uspto-grants-2014_08
Patent number
US08803420B2

Reaction notes

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