1,4-Dibromobenzene → methyl (S)-3-(4-bromophenyl)-2-hydroxypropionate

HRID 910292

反応式

HRID 910292 の反応式
C([Li])(C)(C)C.Br[C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1.[Cu](C#N)C#N.[C:19]([O:24][CH3:25])(=[O:23])[C@H:20]1[O:22][CH2:21]1.[Cl-].[NH4+]>CCCCC>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:21][C@H:20]([OH:22])[C:19]([O:24][CH3:25])=[O:23])=[CH:8][CH:9]=1

参加物

7

反応物 5

HCID 78041,4-DibromobenzeneHCID 25517Ammonium ChlorideHCID 10942355Methyl (2S)-2-oxiranecarboxylateHCID 178418260HCID 178418260、化合物HCID 178418306HCID 178418306、化合物

生成物 1

HCID 39359925methyl (S)-3-(4-bromophenyl)-2-hydroxypropionate収率 133.4%

試薬・触媒・溶媒 1

HCID 8003Pentane溶媒

反応条件

温度
-30 °C

実験手順

100 ml (170 mmol) of a 1.7 M solution of tert-butyllithium in pentane are added dropwise to a solution of 48 g (204 mmol) of 1,4-dibromobenzene in 160 ml of tert-butyl dimethyl ether, cooled to −30° C., followed by addition of 7.3 g (82 mmol) of copper cyanide. The reaction medium is stirred for 15 minutes and a solution of 6 ml (68 mmol) of (S)-methyl glycidate in 10 ml of tert-butyl dimethyl ether is then added. After stirring for 20 minutes at −30° C., the reaction medium is hydrolysed with 150 ml of saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase is washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with heptane, and the polarity is then increased up to a 6/4 heptane/ethyl acetate mixture. 23.5 g (44%) of methyl 3-(4-bromophenyl)-2(S)-hydroxypropanoate are obtained.

後処理

  1. stirringAfter stirring for 20 minutes at −30° C.
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica
  9. washeluted with heptane
  10. temperaturethe polarity is then increased up to a 6/4 heptane/ethyl acetate mixture

出典と根拠

ORDレコード
ord-c044be1b64664c599a14b5eb357fd1ea
出典データセット
uspto-grants-2011_09
特許番号
US08022079B2

関連ノート

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