反応式
[C:1](=O)([O-])[O-:2].[K+].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([F:15])[CH:9]=1.Cl[C:17]1[CH:22]=[CH:21][CH:20]=[C:19](F)[C:18]=1[OH:24].FC1C=CC([N+]([O-])=O)=CC=1.ClC1[CH:41]=[CH:40][C:39]([OH:42])=C(F)C=1Cl.[OH-].[Na+].[Na+].[Cl-]>CS(C)=O>[CH3:1][O:2][C:39](=[O:42])[CH:40]([O:24][C:18]1[CH:19]=[CH:20][C:21]([O:14][C:11]2[CH:12]=[CH:13][C:8]([Cl:7])=[CH:9][C:10]=2[F:15])=[CH:22][CH:17]=1)[CH3:41]参加物
反応物 7
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 100 °C
実験手順
To a stirred mixture of potassium carbonate (25.04 g; 0.18 mol) in DMSO (200 ml) under an argon atmosphere was added an 8:2 mixture (25 g; 0.171 mol) (from Step 2A) of 4-chloro-2-fluorophenol (~20 g; 0.136 mol) and 2-chloro-6-fluorophenol (~5 g; 0.034 mol). To this mixture was added 4-fluoronitrobenzene (18.05 g; 0.128 mol) and the resulting mixture stirred at 100° C. for 30 minutes. At the end of this time, g.c. showed that the mixture contained (peak areas) ~10% of 2-chloro-6-fluorophenol, ~3% of a dichlorofluorophenol, a trace of 4-chloro-2-fluorophenol, and a single product peak. This mixture was poured into aqueous base (~1% NaOH) and the resulting mixture extracted with ether (2×300 ml). The ether extracts were combined, washed with water (an emulsion formed which required a little saturated aqueous NaCl to break), dried (MgSO4) and the solvent removed to give an orange-red oil (34 g). 19F NMR (CDCl3) showed that essentially a single isomer to be present. The material was subjected to Kugelrohr distillation (oven temp.=135°-145°) to give the desired product as a light yellow oil (32 g): RI=1.6038 @ 25° C. Recrystallization from hexane (freezer) gave the product as a white solid: m.p.=55°-57°C.
後処理
- extractionthe resulting mixture extracted with ether (2×300 ml)
- washwashed with water (an emulsion
- customformed which
- dry with materialdried (MgSO4)
- customthe solvent removed
出典と根拠
- ORDレコード
- ord-47f840839b864732a6ec79a88341f0f5
- 出典データセット
- uspto-grants-1987_02
- 特許番号
- US04642338
関連ノート
読み込み中…