Azobisisobutyronitrile → Ethyl 6-(4-fluorophenyl)-2-(bromomethyl)nicotinate

HRID 494201Notes

Reaction equation

HRID 494201 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]([CH3:19])[N:9]=2)=[CH:4][CH:3]=1.[Br:20]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]([CH2:19][Br:20])[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 11345961Ethyl 6-(4-fluorophenyl)-2-methylpyridine-3-carboxylate

Product 1

HCID 69039595Ethyl 6-(4-fluorophenyl)-2-(bromomethyl)nicotinateYield 35.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Ethyl 6-(4-fluorophenyl)-2-methylnicotinate (82 mg, 0.32 mmol), N-bromosuccinimide (67 mg, 0.38 mmol) and AIBN (5 mg, 0.032 mmol) in carbon tetrachloride (7 ml) were irradiated (150W lamp) for 6 h then cooled to room temperature. The solid was filtered off and the filtrate concentated and purified by SPE chromatography to give the title compound (38 mg) as a 5:1 mixture with the dibrominated product. 1H NMR (250 MHz, CDCl3) δ (ppm): 8.32 (d, 1H), 8.11 (dd, 2H), 7.68 (d, 1H), 7.15 (t, 2H), 5.09 (s, 2H), 4.45 (q, 2H), 1.45 (t, 3H).

Workup

  1. filtrationThe solid was filtered off
  2. customthe filtrate concentated and purified by SPE chromatography

Sources & evidence

ORD record
ord-5e360ff95c6f4045a21a6b3d650c00f6
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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