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

HRID 2065736노트

반응식

HRID 2065736 반응식
[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]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 68606931HCID 68606931, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
110 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d6d07fa856a2452187d218b821a7811b
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288552B2

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