1-Bromo-4-methoxy-2-methylbenzene → (2-Fluoro-4-methoxyphenyl)(4-methoxy-2-methylphenyl)methanol

HRID 1816395

반응식

HRID 1816395 반응식
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[CH3:15].[F:16][C:17]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:18]=1[CH:19]=[O:20]>C1COCC1>[F:16][C:17]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:18]=1[CH:19]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[CH3:15])[OH:20]

참가 물질

5

반응물 3

HCID 1179151-Bromo-4-methoxy-2-methylbenzeneHCID 27348732-Fluoro-4-methoxybenzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 22493723(2-Fluoro-4-methoxyphenyl)(4-methoxy-2-methylphenyl)methanol수율 78.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

n-Butyllithium (2.5 M, 44.0 mL) was added dropwise into a cold (−78° C.) solution of 1-bromo-4-methoxy-2-methylbenzene (22.0 g, 109.4 mmol), and THF (150 mL). The reaction mixture was stirred at −78° C. for 3 h, and then 2-fluoro-4-methoxybenzaldehyde (16.8 g, 109.4 mmol) in THF (10 mL) was added. The mixture was allowed to warm up to 0° C. stirred for 10 min, and then quenched with aqueous ammonium chloride. The mixture was poured into water, acidified with HCl (2N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (hexanes/EtOAc 3/1) gave (2-fluoro-4-methoxyphenyl)(4-methoxy-2-methylphenyl)methanol as a yellow oil (23.6 g, 78% yield). The product was dissolved in acetone (150 mL), cooled to 10° C. and Jones Reagent (79.7 mL) was added dropwise. The reaction stirred for poured into water and extracted with ethyl ether. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (hexanes/EtOAc 3/1) gave a yellow oil (23.6 g, 78% yield, m.p. 88-90° C.); MS m/e 275 (M+H)+.

후처리

  1. temperatureto warm up to 0° C.
  2. stirringstirred for 10 min
  3. customquenched with aqueous ammonium chloride
  4. additionThe mixture was poured into water
  5. extractionextracted with EtOAc
  6. dry with materialThe organic extracts were dried over MgSO4
  7. customEvaporation and purification by flash chromatography (hexanes/EtOAc 3/1)

출처 및 근거

ORD 기록
ord-358b7ac9b0164d6282a2123afc1eff0c
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06884814B2

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