Methyl iodide → 1-(4-Bromo-2-fluorophenyl)ethanol

HRID 1476184노트

반응식

HRID 1476184 반응식
C[Mg]I.[Mg].[CH3:5]I.[Br:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[C:10]([F:16])[CH:9]=1>C(OCC)C>[Br:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]([OH:13])[CH3:5])=[C:10]([F:16])[CH:9]=1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 5462224MagnesiumHCID 178418373HCID 178418373, 화합물

생성물 1

HCID 596944341-(4-Bromo-2-fluorophenyl)ethanol

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a ice-cold solution of methyl magnesium iodide prepared from magnesium (1.7 g, 73.88 mmoles) and methyl iodide (4.58 ml, 73.88 mmoles) in diethyl ether (50 ml), 4-bromo-2-fluorobenzaldehyde (5 g, 24.62 mmoles) in diethyl ether (10 ml) was added and warmed to room temperature. After 12 h, the reaction mixture was cooled to 0° C., quenched with dilute HCl and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as red colour liquid (5 g, 94% yield). 1H-NMR (δ ppm, CDCl3, 400 MHz): δ 7.40(t, J=8.2Hz, 1H), 7.30(dd, J=8.3,1.7Hz, 1H), 7.21(dd, J=9.9,1.9Hz, 1H), 5.17(q, J=6.4Hz, 1H), 1.49(d, J=6.5Hz, 3H).

후처리

  1. additionwas added
  2. temperaturethe reaction mixture was cooled to 0° C.
  3. customquenched with dilute HCl
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b15a8c786cee446fa7ce50edf0b526ac
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018375B2

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