Water → 4-(Difluoromethoxy)-3,5-dimethoxybenzaldehyde

HRID 468693노트

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HRID 468693 반응식
Cl[C:2]([F:8])([F:7])C(OC)=O.O[C:10]1(OC)[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]1[O:18][CH3:19].[C:22](=O)([O-])[O-:23].[K+].[K+].[OH2:28]>CN(C=O)C>[F:7][CH:2]([F:8])[O:28][C:10]1[C:11]([O:18][CH3:19])=[CH:12][C:13]([CH:14]=[O:15])=[CH:16][C:17]=1[O:23][CH3:22]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 73935Methyl chlorodifluoroacetateHCID 866503554-Hydroxy-3,4-dimethoxybenzaldehyde

생성물 1

HCID 7105984-(Difluoromethoxy)-3,5-dimethoxybenzaldehyde수율 39%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
67.5 °C

실험 절차

Methyl chlorodifluoroacetate (0.58 mL, 5.5 mmol) was added to a suspension of 4-hydroxy-3,4-dimethoxybenzaldehyde (0.50 g, 2.7 mmol) and potassium carbonate (0.76 g, 5.5 mol) in DMF (5.0 mL). The suspension was heated to 65-70° C. for 16 h and the suspension was diluted with water. The aqueous phase was extracted with EtOAc and the combined organic fractions were washed with saturated aqueous NaHCO3, water, brine, dried and concentrated. The crude product was recrystallised from EtOAc/petrol providing 4-(difluoromethoxy)-3,5-dimethoxybenzaldehyde (0.25 g, 39%) as a colourless crystalline solid; mp 113-115° C.; δH (400 MHz, CDCl3) 3.95 (s, 6H, OCH3), 6.65 (t, J=74 Hz, 1H, OCHF2), 7.15 (s, 2H, H2, H6), 9.91 (s, 1H, CHO); δC (100 MHz, CDCl3) δ6.5, 106.3, 116.2 (t, J=256 Hz), 134.1, 153.5, 190.8; νmax 831, 1048, 1099, 1330, 1600, 1699, 2854 cm−1.

후처리

  1. extractionThe aqueous phase was extracted with EtOAc
  2. washthe combined organic fractions were washed with saturated aqueous NaHCO3, water, brine
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was recrystallised from EtOAc/petrol

출처 및 근거

ORD 기록
ord-82ff59ce80314f98b1f58463600fd8da
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08624056B2

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