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

HRID 724633

반응식

HRID 724633 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1d742bfcfbad42edb21b57e3f9c1a024
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141596B2

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