Dimethyl Sulfate → 3-Bromo-2,5-difluoro-4-methoxybenzaldehyde

HRID 2212595

반응식

HRID 2212595 반응식
[Br:1][C:2]1[C:3]([F:12])=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[OH:10])[CH:5]=[O:6].[C:13](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O.C(OC(=O)C)C>CN(C=O)C>[Br:1][C:2]1[C:3]([F:12])=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[O:10][CH3:13])[CH:5]=[O:6]

참가 물질

6

반응물 4

HCID 6497Dimethyl SulfateHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 21966468HCID 21966468, 화합물

생성물 1

HCID 219664313-Bromo-2,5-difluoro-4-methoxybenzaldehyde수율 53,666%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-bromo-2,5-difluoro-4-hydroxybenzaldehyde (48.4 g, 0.193 mmol) in DMF (200 mL) was added potassium carbonate (40.0 g) and dimethylsulfate (27.4 mL). The reaction mixture was stirred at room temperature overnight. The reaction was diluted wit ethylacetate and washed successively with water and brine, dried over magnesium sulfate, filtered and evaporated. The residue was triturated with hexane to afford 26 g of 3-bromo-2,5-difluoro-4-methoxy benzaldehyde. The mother liquor was evaporated and chromatographed on silica gel (0–10% ethyl acetate in hexane) to give 10.86 g of more product. (38% overall yield from 2,5-dinitrophenol).

후처리

  1. washwashed successively with water and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was triturated with hexane

출처 및 근거

ORD 기록
ord-c80210c2957f425796ba0b687f48b6f0
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07102000B2

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