2,4-Difluorophenol → (S)-benzyl 4-(2,4-difluorophenoxy)-3-oxobutan-2-ylcarbamate

HRID 13220ノート

反応式

HRID 13220 の反応式
Br[CH2:2][C:3](=[O:17])[C@@H:4]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:5].[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[OH:26].[F-].[K+]>CN(C=O)C.ClCCl.O>[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[O:26][CH2:2][C:3](=[O:17])[C@@H:4]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:5]

参加物

7

反応物 3

HCID 1230512,4-DifluorophenolHCID 522689Potassium FluorideHCID 15485144(S)-benzyl 4-bromo-3-oxobutan-2-ylcarbamate

生成物 1

HCID 59339874(S)-benzyl 4-(2,4-difluorophenoxy)-3-oxobutan-2-ylcarbamate収率 94.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of (S)-benzyl 4-bromo-3-oxobutan-2-ylcarbamate (prepared according to R. V. Hoffman et al., J. Org. Chem. 2001, 66, 5790-5795) (600 mg, 2.00 mmol), 2,4-difluorophenol (312 mg, 2.40 mmol) and potassium fluoride (380 mg, 6.54 mmol) in DMF (4 mL) was stirred at r.t. for 17 h. Water (15 mL) and dichloromethane (3 mL) were added and the mixture was stirred for 30 min. The mixture was added to a phase separator. The water phase was once more stirred with dichloromethane (3 mL), and added to the phase separator. The organic phases were concentrated and the residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 3/1) to give the title compound as a white solid (658 mg, 94% yield).

後処理

  1. stirringthe mixture was stirred for 30 min
  2. additionThe mixture was added to a phase separator
  3. additionadded to the phase separator
  4. concentrationThe organic phases were concentrated
  5. customthe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 3/1)

出典と根拠

ORDレコード
ord-fe4251190ce44f28a6e56c60c003be12
出典データセット
uspto-grants-2010_06
特許番号
US07728030B2

反応ノート

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