Triethylamine → 2-[(4-Bromo-2-fluorophenyl)iminomethyl]-3-methylphenol

HRID 558079

反応式

HRID 558079 の反応式
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[OH:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:12]=1[CH:13]=O.C(N(CC)CC)C>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]=[CH:13][C:12]2[C:15]([CH3:19])=[CH:16][CH:17]=[CH:18][C:11]=2[OH:10])=[C:4]([F:9])[CH:3]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 1230504-Bromo-2-fluoroanilineHCID 5851742-Hydroxy-6-methylbenzaldehyde

生成物 1

HCID 1363420412-[(4-Bromo-2-fluorophenyl)iminomethyl]-3-methylphenol収率 99.7%

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒HCID 1140Toluene溶媒

実験手順

A solution of 4-bromo-2-fluoroaniline (19.6 g, 103.16 mmol), 2-hydroxy-6-methyl-benzaldehyde (14.03 g, 103.16 mmol) and p-toluenesulfonic acid (188 mg, 0.99 mmol) in toluene (300 mL) was heated to reflux in a Dean-Stark apparatus for 1 h and then allowed to cool to ambient temperature. After adding triethylamine (0.8 mL) the reaction mixture was concentrated to give the crude title compound (31.7 g, 99%) which was used without further purification. Data: 1H-NMR (400 MHz, CDCl3) δ 2.52 (s, 3H), 6.72 (d, J=7.6 Hz, 1H), 6.88 (d, J=8.6 Hz, 1H), 5.15 (t, J=7.8 Hz, 1H), 7.26-7.38 (m, 3H), 9.03 (s, 1H), 13.63 (s, 1H).

後処理

  1. temperatureto reflux in a Dean-Stark apparatus for 1 h
  2. concentrationwas concentrated

出典と根拠

ORDレコード
ord-b0258ddc93b44685815189650c94b970
出典データセット
uspto-grants-2011_11
特許番号
US08063037B2

関連ノート

読み込み中…