Carbon Dioxide → 2,3-Dichloro-6-iodobenzoic acid

HRID 321994

反応式

HRID 321994 の反応式
C([Li])CCC.C(NC(C)C)(C)C.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=1[Cl:21].[C:22](=[O:24])=[O:23]>C1COCC1.O>[Cl:21][C:15]1[C:14]([Cl:13])=[CH:19][CH:18]=[C:17]([I:20])[C:16]=1[C:22]([OH:24])=[O:23]

参加物

7

反応物 4

HCID 280Carbon DioxideHCID 7912DiisopropylamineHCID 88591Benzene, 1,2-dichloro-4-iodo-HCID 178418339Butyllithium

生成物 1

HCID 220088162,3-Dichloro-6-iodobenzoic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

n-Butyllithium (1.45M solution in hexane, 19.4 mmol, 13.4 ml) was added dropwise to a stirred solution of diisopropylamine (21.4 mmol, 3.0 ml) in THF (90 ml) at 0° C. After 30 minutes, the solution was cooled to −78° C. and a solution of 1,2-dichloro-4-iodobenzene (5.30 g, 19.4 mmol) in TIF (10 ml) was added dropwise. After 10 minutes, solid carbon dioxide was added cautiously and the allowed to warm to room temperature over 16 h. The mixture was diluted with water and extracted twice with ethyl acetate. The aqueous layer was acidified with dilute aqueous hydrochloric acid and then extracted twice with ethyl acetate. The extracts were dried over sodium sulphate and evaporated to give the title compound as a yellow solid (3.59 g). 300 MHz 1H NMR (d6-DMSO) 11.5 (1H, br.s), 7.82 (1H, d, J 8.4 Hz), 7.44 (1H, d, J 8.4 Hz).

後処理

  1. waitAfter 10 minutes
  2. temperatureto warm to room temperature over 16 h
  3. extractionextracted twice with ethyl acetate
  4. extractionextracted twice with ethyl acetate
  5. dry with materialThe extracts were dried over sodium sulphate
  6. customevaporated

出典と根拠

ORDレコード
ord-c0a86ed9408c4d2a90ae053d191ec308
出典データセット
uspto-grants-2001_04
特許番号
US06211189B1

関連ノート

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