Water → HCID 54157105、化合物

HRID 439563ノート

反応式

HRID 439563 の反応式
[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]

参加物

8

反応物 6

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

生成物 1

HCID 54157105HCID 54157105、化合物収率 41%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-388bda3eb5334bfeb6683f9ceba816df
出典データセット
uspto-grants-1996_05
特許番号
US05514711

反応ノート

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