Ammonium Chloride → 1-(4-Chloro-3-fluorophenyl)ethan-1-ol

HRID 1436448

반응식

HRID 1436448 반응식
[CH3:1][Mg]Br.[Cl:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[F:13].[NH4+].[Cl-]>O1CCCC1>[Cl:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]([OH:10])[CH3:1])=[CH:7][C:6]=1[F:13]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 27249854-Chloro-3-FluorobenzaldehydeHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 219347441-(4-Chloro-3-fluorophenyl)ethan-1-ol수율 100%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Methylmagnesium bromide (22.5 mL, 31.5 mmol; 1.4 M solution in toluene/tetrahydrofuran) was added dropwise to a solution of 4-chloro-3-fluorobenzaldehyde (5.0 g, 31.5 mmol) in 100 mL of dry tetrahydrofuran at −78° C. over 15 min. The reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured into saturated NH4Cl (100 mL). The aqueous layer was extracted with diethyl ether (3×150 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 1-(4-chloro-3-fluorophenyl)ethanol (5.50 g, 100%) as a yellow oil which was used in the next step without further purification, MS (ES) m/z 175 [M+H+].

후처리

  1. extractionThe aqueous layer was extracted with diethyl ether (3×150 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3fefa5aa44a8429f9e3956cdbd31434a
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618990B2

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