1,8-Diaminonaphthalene → 2-(3-Bromophenyl)-2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborine

HRID 1846037

反応式

HRID 1846037 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([B:8](O)O)[CH:5]=[CH:6][CH:7]=1.[C:11]1([NH2:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][C:19]=2[NH2:21])[CH:14]=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([B:8]2[NH:22][C:11]3[C:20]4[C:15]([CH:14]=[CH:13][CH:12]=3)=[CH:16][CH:17]=[CH:18][C:19]=4[NH:21]2)[CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 680671,8-DiaminonaphthaleneHCID 2734318(3-Bromophenyl)boronic acid

生成物 1

HCID 533844122-(3-Bromophenyl)-2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborine収率 54%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 3-bromobenzene boronic acid (20 g, 0.1 mol) and naphthalene-1,8-diamine (17.3 g, 0.11 mol) in anhydrous toluene (600 mL) was heated to reflux for 16 hours. The reaction mixture was cooled to room temperature, then concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with petroleum ether:EtOAc 5:1 to afford the title compound as a grey solid in 54% yield, 23 g.

後処理

  1. temperatureto reflux for 16 hours
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography
  4. washeluting with petroleum ether:EtOAc 5:1

出典と根拠

ORDレコード
ord-562e58f8917f4ef58c890f9fa3461faf
出典データセット
uspto-grants-2015_02
特許番号
US08952008B2

関連ノート

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