Potassium Carbonate → {2-[(3-Bromo-4-chloro-benzoyl)-methyl-amino]-phenoxy}-acetic acid methyl ester

HRID 448861ノート

反応式

HRID 448861 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[C:5]([N:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])[CH3:8])=[O:6].[CH3:20][O:21][C:22](=[O:25])[CH2:23]Br.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:20][O:21][C:22](=[O:25])[CH2:23][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[N:7]([C:5](=[O:6])[C:4]1[CH:16]=[CH:17][C:18]([Cl:19])=[C:2]([Br:1])[CH:3]=1)[CH3:8]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 686031173-bromo-4-chloro-N-(2-hydroxy-phenyl)-N-methyl-benzamide

生成物 1

HCID 68602946{2-[(3-Bromo-4-chloro-benzoyl)-methyl-amino]-phenoxy}-acetic acid methyl ester収率 92.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 3-bromo-4-chloro-N-(2-hydroxy-phenyl)-N-methyl-benzamide (442 mg, 1.3 mmol), methylbromoacetate (0.247 mL, 2.6 mmol) and K2CO3 (717 mg, 5.2 mmol) was heated in DMF (8 mL) at 80° C. for 5 hrs. After cooling to room temperature, the mixture was partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried over Na2SO4, then purified by silica gel column chromatography eluted with ethyl acetate/hexane (1/4) to yield {2-[(3-bromo-4-chloro-benzoyl)-methyl-amino]-phenoxy}-acetic acid methyl ester (495 mg). MS [M+H]+: 413.9; tR=2.75 min. (method 1)

後処理

  1. customthe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. custompurified by silica gel column chromatography
  6. washeluted with ethyl acetate/hexane (1/4)

出典と根拠

ORDレコード
ord-dc19c1b9147447778c50b5771a0b706d
出典データセット
uspto-grants-2013_07
特許番号
US08481738B2

反応ノート

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