Benzyl chloroformate → 914452-60-1

HRID 62048ノート

反応式

HRID 62048 の反応式
[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

参加物

7

反応物 3

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

生成物 1

HCID 25018359914452-60-1収率 98.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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]+).

後処理

  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

出典と根拠

ORDレコード
ord-162bbeab3ef04fc09eb09fd15ae8e156
出典データセット
uspto-grants-2016_09
特許番号
US09445594B2

反応ノート

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