Benzoyl Peroxide → HCID 22241465, compound

HRID 892156Notes

Reaction equation

HRID 892156 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([F:13])[CH:6]=[C:7]([F:12])[CH:8]=2)[N:3]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:32]NC(=O)CCC(N)=O>C(Cl)(Cl)(Cl)Cl>[F:12][C:7]1[CH:8]=[C:9]2[C:4](=[C:5]([F:13])[CH:6]=1)[N:3]=[C:2]([CH2:1][Br:32])[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 9834204N-BromosuccinamideHCID 22241285HCID 22241285, compound

Product 1

HCID 22241465HCID 22241465, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 2-methyl-6,8-difluoroquinoline (0.147 g, 0.820 mmoles, Example 26a), benzoyl peroxide (9.93 mg, 0.0410 mmoles), and N-bromosuccinamide (0.168 g, 0.943 mmoles) in carbon tetrachloride (20 mL) is heated to reflux for 18 hours. The reaction is concentrated and the resulting residue purified by column chromatography (silica, 3:1 CH2Cl2:hexane, then CH2Cl2) to yield the title compound as a white solid. MS (ESI) 258, 260 (M+H)+, Br pattern.

Workup

  1. temperatureto reflux for 18 hours
  2. concentrationThe reaction is concentrated
  3. customthe resulting residue purified by column chromatography (silica, 3:1 CH2Cl2

Sources & evidence

ORD record
ord-05791a76b10f451ab52a8bfe6b1c4722
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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