Potassium Carbonate → Benzoic acid, 5-amino-2-chloro-4-methyl-, methyl ester

HRID 2065736ノート

反応式

HRID 2065736 の反応式
[CH3:1][O:2][C:3](=[O:13])[C:4]1[C:9](Br)=[C:8]([NH2:11])[CH:7]=[CH:6][C:5]=1[Cl:12].[C:14](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([NH2:11])[C:7]([CH3:14])=[CH:6][C:5]=1[Cl:12]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 68606931HCID 68606931、化合物

生成物 1

HCID 57423009Benzoic acid, 5-amino-2-chloro-4-methyl-, methyl ester収率 71.6%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

To a solution of 5-amino-6-bromo-2-chloro-benzoic acid methyl ester (0.5 g, 1.89 mmol) in dioxane (10 ml) and water (1 ml) was added potassium carbonate (0.784 g, 5.67 mmol), PdCl2(dppf) (0.54 g, 0.189 mmol) and trimethyl boroxine (0.276 ml, 1.985 mmol). The mixture was stirred at 110° C. for 18 hours, then cooled to room temperature and filtered. The filtrate was concentrated to dryness under reduced pressure. Purification of the residue by flash chromatography (hexanes:EtOAc 8:2) gave 0.270 g (71%) of 5-amino-2-chloro-4-methyl-benzoic acid methyl ester as a tan solid.

後処理

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated to dryness under reduced pressure
  4. customPurification of the residue by flash chromatography (hexanes:EtOAc 8:2)

出典と根拠

ORDレコード
ord-d6d07fa856a2452187d218b821a7811b
出典データセット
uspto-grants-2012_10
特許番号
US08288552B2

反応ノート

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