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

HRID 661652ノート

反応式

HRID 661652 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-9d0fa683945041bcb8246647df2f2e5c
出典データセット
uspto-grants-2011_12
特許番号
US08084614B2

反応ノート

読み込み中…