Water → HCID 54157105, 화합물

HRID 439563노트

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HRID 439563 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([OH:9])[C:3]=1[O:10][CH3:11].F[C:13]1([O:21][CH3:22])C(O)=CC(F)=CC1.B(Br)(Br)Br.[CH:27](N(C(C)C)CC)(C)C.[CH3:36][O:37]CCl.[OH2:40]>C(Cl)Cl>[F:1][C:2]1[C:3]([O:10][CH2:11][O:37][CH3:36])=[C:4]([O:9][CH2:13][O:21][CH3:22])[C:5]([F:8])=[CH:6][C:7]=1[CH:27]=[O:40]

참가 물질

8

반응물 6

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 25134Boron tribromideHCID 81531DiisopropylethylamineHCID 5894393,6-Difluoro-2-methoxyphenolHCID 67745008HCID 67745008, 화합물

생성물 1

HCID 54157105HCID 54157105, 화합물수율 41%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

1, 4-Difluoro-2-methoxy-3-hydroxybenzene (1.60 g, 9.99 mmol) was converted into 2, 5-difluoro-2-methoxy-3-hydroxybenzene (610 mg, 33%) according to the method as described in L. Kirk et al., J. Org. Chem., 51, 4073 (1986). This compound (350 mg, 1.86 mmol) was allowed to react with 1M solution of boron tribromide in methylene chloride in the same manner as in Example 2. The crude product obtained above was dissolved in methylene chloride (2 ml), and diisopropylethylamine (0.4 ml, 2.3 mmol) and methoxymethyl chloride (0.45 ml, 6.0 mmol) were added to the solution, which was stirred at room temperature for 1 hour. The reaction mixture was mixed with water, extracted with ethyl acetate-hexane and the extract was concentrated in vacuo. The residue was chromatographed on a column of silica gel to give 2, 5-difluoro-3, 4-bis (methoxymethyloxy) benzaldehyde (200 mg, 41%).

후처리

  1. customThe crude product obtained
  2. extractionextracted with ethyl acetate-hexane
  3. concentrationthe extract was concentrated in vacuo
  4. customThe residue was chromatographed on a column of silica gel

출처 및 근거

ORD 기록
ord-388bda3eb5334bfeb6683f9ceba816df
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05514711

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