1,1'-Biphenyl, 4-(bromomethyl)- → 1-(2-Biphenyl-4-yl-1-phenyl-ethyl)-1H-benzotriazole

HRID 724633

反応式

HRID 724633 の反応式
[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:26][CH:25]=1>O1CCCC1>[C:27]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:26]=[CH:25][C:24]([CH2:23][CH:1]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[N:9]2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:29][CH:28]=1

参加物

5

反応物 3

HCID 2577161,1'-Biphenyl, 4-(bromomethyl)-HCID 5212121-Benzyl-1H-benzotriazoleHCID 178418339Butyllithium

生成物 1

HCID 218795131-(2-Biphenyl-4-yl-1-phenyl-ethyl)-1H-benzotriazole収率 83%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

A solution of 1-benzyl-1H-1,2,3-benzotriazole (750 mg, 3.6 mmol) in tetrahydrofuran (36 mL) was cooled to −78° C. and treated with n-butyllithium (2.8 mL, 1.6 M in hexanes) dropwise. The reaction mixture was stirred at −78° C. for 10 min and 4-bromomethyl-biphenyl (1.0 g, 4.1 mmol) in tetrahydrofuran (4 mL) was added dropwise. The reaction mixture was stirred at −78° C. for 1 h, quenched with sat. ammonium chloride (100 mL), and extracted with ethyl acetate (150 mL). The organic layer was separated and washed with brine (50 mL), dried with sodium sulfate, filtered, and concentrated to a white solid. This material was triturated with diethyl ether (2×50 mL) to yield the desired product (1.12 g, 83%). LCMS found for C26H22N3 (M+H)+: m/z=376.

後処理

  1. stirringThe reaction mixture was stirred at −78° C. for 1 h
  2. customquenched with sat. ammonium chloride (100 mL)
  3. extractionextracted with ethyl acetate (150 mL)
  4. customThe organic layer was separated
  5. washwashed with brine (50 mL)
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to a white solid
  9. customThis material was triturated with diethyl ether (2×50 mL)

出典と根拠

ORDレコード
ord-1d742bfcfbad42edb21b57e3f9c1a024
出典データセット
uspto-grants-2006_11
特許番号
US07141596B2

関連ノート

読み込み中…