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

HRID 1643764ノート

反応式

HRID 1643764 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-0b516d6936f74020b0b1d86d2225a61a
出典データセット
uspto-grants-2012_02
特許番号
US08119624B2

反応ノート

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