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Acetic Acid → Methyl 4-(Bromomethyl)-2,6-dichloronicotinate

HRID 922052
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HRID 922052 반응식
[CH3:1][O:2][C:3]([C:5]1[C:6]([Cl:13])=[N:7][C:8]([Cl:12])=[CH:9][C:10]=1[CH3:11])=[O:4].[Br:14]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C.C(O)(=O)C>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:6]([Cl:13])=[N:7][C:8]([Cl:12])=[CH:9][C:10]=1[CH2:11][Br:14])=[O:4]
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참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 46911843Methyl 2,6-dichloro-4-methylnicotinate

생성물 1

HCID 86664328Methyl 4-(Bromomethyl)-2,6-dichloronicotinate수율 72.2%

시약·촉매·용매 1

HCID 5943
Carbon Tetrachloride
용매

실험 절차

To a solution of 5.3 g (24.1 mmol) 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid methylester in CCl4 (92 ml) were added 3.1 g (26.5 mmol) N-Bromosuccinimide, 395 mg (2.4 mmol) AIBN and 1.45 ml (25.3 mmol) acetic acid. The mixture was irradiated with a 200 W Wolfram lamp at 60° C. for 24 h. Subsequently the mixture was filtered through celite and the filtrate was concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 97:3) provided 5.2 g of a mixture of 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid methylester and 4-(bromomethyl)-2,6-dichloro-pyridine-3-carboxylic acid methylester which was used in subsequent reactions without further purification.

후처리

  1. filtrationSubsequently the mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customPurification of the residue by CC (hexane/EtOAc 97:3)

출처 및 근거

ORD 기록
ord-c56349b03be741dc97890034a3f8c417
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09278103B2

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