Hydrochloric Acid → 2-(5-Bromo-2-chlorophenyl)propan-2-ol

HRID 2110800

反応式

HRID 2110800 の反応式
COC(=O)[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[Cl:11].[CH3:13][Mg]Br.Cl.C([O:19][CH2:20][CH3:21])C>C1COCC1>[Br:10][C:8]1[CH:7]=[CH:6][C:5]([Cl:11])=[C:4]([C:20]([OH:19])([CH3:21])[CH3:13])[CH:9]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 842098Methyl 5-bromo-2-chlorobenzoateHCID 178418573HCID 178418573、化合物

生成物 1

HCID 685596932-(5-Bromo-2-chlorophenyl)propan-2-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 5-bromo-2-chloro-benzoic acid methyl ester (5 g) in diethyl ether (200 mL) cooled to −70° C. is added 3 M methylmagnesium bromide in THF (20 mL) dropwisely. The solution is stirred at −78° C. for 2 h and allowed to warm to room temperature for 16 hours. The solution is cooled to 0° C. and 1 N HCl (100 mL) is added dropwisely. The mixture is extracted with EtOAc (2×150 mL). The combined organic layer is washed with brine, dried over sodium sulfate, filtered and evaporated in vacuo. The residue is chromatographed on silica gel eluting with 20% EtOAc in heptane to afford 2-(5-bromo-2-chloro-phenyl)-propan-2-ol (4.56 g). MS: 250 (M+H); 1H NMR (300 MHz, CDCl3) □7.8 (m, 1H); 7.5 (m, 1H); 7.2 (m, 1H); 4.4 (s, 1H); 1.6 (s, 6H).

後処理

  1. temperatureto warm to room temperature for 16 hours
  2. temperatureThe solution is cooled to 0° C.
  3. extractionThe mixture is extracted with EtOAc (2×150 mL)
  4. washThe combined organic layer is washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue is chromatographed on silica gel eluting with 20% EtOAc in heptane

出典と根拠

ORDレコード
ord-35c3a37c898144199f49264c64bf807d
出典データセット
uspto-grants-2009_04
特許番号
US07517889B2

関連ノート

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