Diisopropylethylamine → 1-Bromo-3-isocyanato-2-methyl-benzene

HRID 523274ノート

反応式

HRID 523274 の反応式
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[Br:13][C:14]1[C:15]([CH3:21])=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[Br:13][C:14]1[CH:20]=[CH:19][CH:18]=[C:16]([N:17]=[C:5]=[O:11])[C:15]=1[CH3:21]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 1235383-Bromo-o-toluidine

生成物 1

HCID 655423311-Bromo-3-isocyanato-2-methyl-benzene収率 229%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

A solution of triphosgene (2.25 g, 7.58 mmol) in toluene (27 mL), cooled in an ice-water bath, was treated slowly with a solution of 3-bromo-2-methylaniline (3.00 g, 16.1 mmol) and DIEA (5.6 mL, 32.2 mmol) in toluene (5.4 mL). The resulting suspension was stirred at room temperature for 2 h. The precipitate was removed by filtration and washed with EtOAc. The combined filtrates were diluted with EtOAc, washed with brine, dried and concentrated to provide 1-bromo-3-isocyanato-2-methylbenzene as a brown oil (3.68 g, 98% yield), used without purification. 1H NMR (400 MHz, DMSO-d6) δ 7.49 (dd, J=8.1, 0.9 Hz, 1H), 7.31 (dd, J=7.9, 0.7 Hz, 1H), 7.15 (td, J=8.0, 0.7 Hz, 1H), 2.38 (s, 3H).

後処理

  1. customThe precipitate was removed by filtration
  2. washwashed with EtOAc
  3. additionThe combined filtrates were diluted with EtOAc
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-80aa8b1a961546129992fd756427e07d
出典データセット
uspto-grants-2016_05
特許番号
US09334290B2

反応ノート

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