Benzyl chloroformate → 914452-60-1

HRID 62048노트

반응식

HRID 62048 반응식
[Cl-].[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH3+:10])=[CH:5][CH:4]=1.[OH-].[Na+].[C:13](Cl)(=[O:22])[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1.O.[Cl-].[Na+].O>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:13](=[O:22])[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:5][CH:4]=1

참가 물질

7

반응물 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 11322024(4-Bromophenyl)methylazanium chloride

생성물 1

HCID 25018359914452-60-1수율 98.1%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

In a 500 mL flask, (4-bromophenyl)methanaminium chloride (10.0 g, 44.9 mmol) and sodium hydroxide (4.00 g, 100 mmol) were dissolved in tetrahydrofuran (80 mL) and water (80 mL). The flask was placed in an ice water bath and benzyl carbonochloridate (7.06 mL, 49.4 mmol) was added dropwise. The reaction was allowed to stir for 3 h. The reaction was then poured into brine solution and extracted with ethyl acetate (3×150 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated to give the title compound as a white solid (14.1 g, 97%): 1H NMR (400 MHz, DMSO-d6) δ 7.88 (t, J=6.1 Hz, 1H), 7.58-7.46 (m, 2H), 7.46-7.27 (m, 5H), 7.23 (d, J=8.2 Hz, 2H), 5.06 (s, 2H), 4.19 (d, J=6.2 Hz, 2H); 13C NMR (101 MHz, DMSO-d6) δ 156.34, 139.19, 137.05, 131.10, 129.22, 128.32, 127.78, 127.73, 119.79, 65.44, 43.22; ESIMS m/z 320 ([M+H]+).

후처리

  1. customThe flask was placed in an ice water bath
  2. extractionextracted with ethyl acetate (3×150 mL)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-162bbeab3ef04fc09eb09fd15ae8e156
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09445594B2

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