Dimethylformamide → HCID 86082491, compound

HRID 659923Notes

Reaction equation

HRID 659923 reaction equation
[C:1]([C:5]1[CH:18]=[CH:17][C:16]2[C:7](=[C:8]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:25]N1C(=O)CCC1=O.CN(C)C=O>O>[Br:25][C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:7]2[C:16]=1[CH:17]=[CH:18][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 86082488HCID 86082488, compound

Product 1

HCID 86082491HCID 86082491, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixed solution of 6.8 g of the above-mentioned 2-tert-butyl-9-phenylanthracene, 4.3 g of N-bromosuccinimide and 60 ml of dimethylformamide was stirred under nitrogen gas stream at room temperature for 2 hours. 50 ml of water was injected thereto to extract 100 ml of dichloromethane therefrom. The organic layer was washed twice in 50 ml of water, dried by magnesium sulfate and thereafter concentrated by evaporation. The organic layer was purified by silica gel column chromatography to obtain 10-bromo-2-tert-butyl-9-phenylanthracene.

Workup

  1. extractionto extract 100 ml of dichloromethane
  2. washThe organic layer was washed twice in 50 ml of water
  3. dry with materialdried by magnesium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe organic layer was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e3690a3bc8694720b2c85b80f4713551
Source dataset
uspto-grants-2011_12
Patent number
US08084146B2

Reaction notes

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