Methoxymethyl-triphenylphosphonium chloride → 2,6-Diisopropyl-4-bromo-beta-methoxystyrene

HRID 924584노트

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HRID 924584 반응식
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH:34]([C:37]1[CH:44]=[C:43]([Br:45])[CH:42]=[C:41]([CH:46]([CH3:48])[CH3:47])[C:38]=1[CH:39]=O)([CH3:36])[CH3:35]>C1COCC1>[CH:34]([C:37]1[CH:44]=[C:43]([Br:45])[CH:42]=[C:41]([CH:46]([CH3:48])[CH3:47])[C:38]=1[CH:39]=[CH:2][O:3][CH3:4])([CH3:36])[CH3:35]

참가 물질

5

반응물 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 2733832Lithium HexamethyldisilazideHCID 574376682,6-Diisopropyl-4-bromobenzaldehyde

생성물 1

HCID 668135662,6-Diisopropyl-4-bromo-beta-methoxystyrene수율 78.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

Methoxymethyl triphenylphosphonium chloride (18.68 g, 54.5 mmol) was suspended in 200 mL of THF at −78° C. Lithium hexamethyldisilazide (1.0 M in THF, 50 mL) was added dropwise. The resulting mixture was warmed up to 0° C. with stirring. After cooling the solution to −78° C. 2,6-diisopropyl-4-bromobenzaldehyde (11.5 g, 42.7 mmol) in 20 mL of THF was added dropwise. The mixture was slowly warmed up to room temperature and continually stirred overnight. After regular work up, the crude product was distilled at 165° C. under vacuum to afford 2,6-diisopropyl-4-bromo-β-methoxystyrene (10 g). This product was dissolved in 20 mL of dioxane and 100 mL of 18% HCl solution and refluxed at 100° C. for 6 h. After regular work up, the crude product was distilled at 160° C. under vacuum to afford 2,6-diisopropyl-4-bromophenylacetaldehyde (7.5 g).

후처리

  1. temperatureAfter cooling the solution to −78° C
  2. temperatureThe mixture was slowly warmed up to room temperature and continually stirred overnight
  3. distillationAfter regular work up, the crude product was distilled at 165° C. under vacuum

출처 및 근거

ORD 기록
ord-43a8bdbc626b46afa381ff43717afd00
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09281483B2

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