Benzoyl Peroxide → HCID 86607511, compound

HRID 1465941Notes

Reaction equation

HRID 1465941 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)[S:14][C:8]=2[C:7]=1[OH:25])=[O:5])[CH3:2].[Br:26]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([Br:26])[C:9]2[CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:24])[F:22])[CH:16]=3)[S:14][C:8]=2[C:7]=1[OH:25])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 67232853HCID 67232853, compound

Product 1

HCID 86607511HCID 86607511, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of 7-hydroxy-2-(3-trifluoromethyl-phenyl)-thieno[3,2-c]pyridine-6-carboxylic acid ethyl ester (example 24.b, 120 mg, 0.32 mmol), N-bromosuccinimide (60 mg, 0.34 mmol), and benzoyl peroxide (7.3 mg, 0.03 mmol) in 0.8 mL of carbon tetrachloride was heated at reflux temperature for 5 hours. The reaction mixture was cooled and chromatographed on silica gel, eluting the desired product with 30% ethyl acetate in hexanes to provide 126 mg of a white solid: MS: (+) m/z 445.9, 447.9 (M+1, 79Br/81Br)

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 5 hours
  3. temperatureThe reaction mixture was cooled
  4. customchromatographed on silica gel
  5. washeluting the desired product with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-59539c7d2d0944abbb26d93089ce5745
Source dataset
uspto-grants-2015_04
Patent number
US09000006B2

Reaction notes

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