Sodium hydride → 2-Chloro-4-(4-chloro-2-fluoro-benzyloxy)-5-methoxy-benzaldehyde

HRID 253458

反応式

HRID 253458 の反応式
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[C:7]([O:11][CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[F:24]>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[F:24])[C:7]([O:11][CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 290002-Chloro-4-hydroxy-5-methoxybenzaldehydeHCID 27365514-Chloro-2-fluorobenzyl bromide

生成物 1

HCID 598038352-Chloro-4-(4-chloro-2-fluoro-benzyloxy)-5-methoxy-benzaldehyde

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-Chloro-4-hydroxy-5-methoxy-benzaldehyde (136, 0.548 g, 2.94 mmol, prepared as described in Example 46, Scheme 45, step 1) was dissolved in N,N-dimethylformamide (40 mL) and sodium hydride (60% dispersion in mineral oil, 0.200 g, 5.00 mmol) was added. After 20 minutes, 1-bromomethyl-4-chloro-2-fluoro-benzene (139, 685 μL, 5.00 mmol) was added to the reaction mixture. The reaction was stirred at room temperature under an atmosphere of nitrogen for 5.5 hours. The reaction was concentrated to dryness in vacuo. The reaction was resuspended in water/saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography, eluting with 5-35% ethyl acetate in hexane give a white solid (140, 0.942 g, 97%), consistent with the desired compound by 1H-NMR.

後処理

  1. concentrationThe reaction was concentrated to dryness in vacuo
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography
  7. washeluting with 5-35% ethyl acetate in hexane
  8. customgive a white solid (140, 0.942 g, 97%)

出典と根拠

ORDレコード
ord-b926d63280ac4b59b2ebad044c849da3
出典データセット
uspto-grants-2011_01
特許番号
US07872018B2

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