Benzoyl Peroxide → Ethyl 2-(bromomethyl)-4-[4-(difluoromethyl)phenoxy]-1-benzofuran-6-carboxylate

HRID 1643764Notes

Reaction equation

HRID 1643764 reaction equation
[F:1][CH:2]([F:25])[C:3]1[CH:24]=[CH:23][C:6]([O:7][C:8]2[C:13]3[CH:14]=[C:15]([CH3:17])[O:16][C:12]=3[CH:11]=[C:10]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:9]=2)=[CH:5][CH:4]=1.C1C(=O)N([Br:33])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)Cl>[Br:33][CH2:17][C:15]1[O:16][C:12]2[CH:11]=[C:10]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:9]=[C:8]([O:7][C:6]3[CH:5]=[CH:4][C:3]([CH:2]([F:1])[F:25])=[CH:24][CH:23]=3)[C:13]=2[CH:14]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 59559977Ethyl 4-[4-(difluoromethyl)phenoxy]-2-methyl-1-benzofuran-6-carboxylate

Product 1

HCID 59560246Ethyl 2-(bromomethyl)-4-[4-(difluoromethyl)phenoxy]-1-benzofuran-6-carboxylateYield 51%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of ethyl 4-[4-(difluoromethyl)phenoxy]-2-methyl-1-benzofuran-6-carboxylate (710 mg, 2.05 mmol) and NBS (438 mg, 2.46 mmol) in CHCl3 (25 mL) was added benzoyl peroxide (49.7 mg, 0.205 mmol). The mixture was refluxed for 14 hours. The solvent was evaporated, and the product was purified via gradient silica gel chromatography using hexanes/EtOAc (100/0 to 70/30) to give the title compound (440 mg, 51%) as a light-yellow solid. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.38 (t, J=7.16 Hz, 3 H) 4.38 (q, J=7.16 Hz, 2 H) 4.53 (s, 2 H) 6.39-6.89 (m, 2 H) 7.07 (d, J=8.48 Hz, 2 H) 7.49 (d, J=8.48 Hz, 2 H) 7.54 (d, J=0.94 Hz, 1 H) 8.01 (s, 1 H).

Workup

  1. temperatureThe mixture was refluxed for 14 hours
  2. customThe solvent was evaporated
  3. customthe product was purified via gradient silica gel chromatography

Sources & evidence

ORD record
ord-0b516d6936f74020b0b1d86d2225a61a
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

Loading…