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

HRID 216272

반응식

HRID 216272 반응식
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

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 842098Methyl 5-bromo-2-chlorobenzoateHCID 178418573HCID 178418573, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7de35ea0c8994387bc7db0953ad1b8b3
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193183B2

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