Potassium Carbonate → 4-[4-Bromo-5-chloro-2-(methyl-o-tolyl-carbamoyl)-phenoxy]-butyric acid tert-butyl ester

HRID 661652노트

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HRID 661652 반응식
[Br:1][C:2]1[C:3]([Cl:20])=[CH:4][C:5]([OH:19])=[C:6]([CH:18]=1)[C:7]([N:9]([CH3:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])=[O:8].C([O-])([O-])=O.[K+].[K+].Br[CH2:28][CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]>CN(C=O)C>[C:34]([O:33][C:31](=[O:32])[CH2:30][CH2:29][CH2:28][O:19][C:5]1[CH:4]=[C:3]([Cl:20])[C:2]([Br:1])=[CH:18][C:6]=1[C:7](=[O:8])[N:9]([CH3:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])([CH3:37])([CH3:36])[CH3:35]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 2757253tert-Butyl 4-bromobutanoateHCID 686026125-bromo-4-chloro-2-hydroxy-N-methyl-N-o-tolyl-benzamide

생성물 1

HCID 686027224-[4-Bromo-5-chloro-2-(methyl-o-tolyl-carbamoyl)-phenoxy]-butyric acid tert-butyl ester수율 82.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

To 5-bromo-4-chloro-2-hydroxy-N-methyl-N-o-tolyl-benzamide (2.6 g, 7.3 mmol) in dry DMF (30 mL), was added K2CO3 (2.0 g, 7.6 mmol), followed by addition of t-butyl 4-bromobutyrate (2.0 g, 8.8 mmol). The mixture was heated at 60° C. for 12 hrs and partitioned between ethyl acetate and water. The organic layer was separated, washed with water and brine, and dried over MgSO4. After filtration, concentration and purification by silica gel column chromatography eluting with ethyl acetate in hexanes (3/7) gave 4-[4-bromo-5-chloro-2-(methyl-o-tolyl-carbamoyl)-phenoxy]-butyric acid tert-butyl ester (3.0 g). MS: 496.3 (M+H); tR=2.81 min (method 1).

후처리

  1. custompartitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration, concentration and purification by silica gel column chromatography
  6. washeluting with ethyl acetate in hexanes (3/7)

출처 및 근거

ORD 기록
ord-9d0fa683945041bcb8246647df2f2e5c
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084614B2

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