Methyltriphenylphosphonium iodide → 1-Fluoro-4-methoxy-2-vinylbenzene

HRID 278050

반응식

HRID 278050 반응식
[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[F:28][C:29]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][C:30]=1[CH:31]=O>O1CCCC1>[CH:31]([C:30]1[CH:33]=[C:34]([O:37][CH3:38])[CH:35]=[CH:36][C:29]=1[F:28])=[CH2:2]

참가 물질

5

반응물 3

HCID 638159Methyltriphenylphosphonium iodideHCID 27348722-Fluoro-5-methoxybenzaldehydeHCID 23665647Potassium tert-butoxide

생성물 1

HCID 114464461-Fluoro-4-methoxy-2-vinylbenzene수율 92.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

39.4 g of methyltriphenylphosphonium iodide and 10.9 g of potassium t-butoxide were suspended in 150 ml of tetrahydrofuran. The resulting suspension was stirred at 0° C. under nitrogen stream for 30 minutes, followed by the dropwise addition thereto of a solution of 10 g of 2-fluoro-5-methoxybenzaldehyde in 20 ml of tetrahydrofuran. The resulting mixture was further stirred for one hour, quenched by the addition of water and extracted with ethyl acetate. The formed organic layer was washed with water and brine successively, dried over anhydrous magnesium sulfate, and evaporated. The resulting residue was subjected to silica gel column chromatography (developer: 5% ethyl acetate/n-hexane) to give 9.1 g of the title compound as a colorless oil.

후처리

  1. additionfollowed by the dropwise addition
  2. stirringThe resulting mixture was further stirred for one hour
  3. customquenched by the addition of water
  4. extractionextracted with ethyl acetate
  5. washThe formed organic layer was washed with water and brine successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated

출처 및 근거

ORD 기록
ord-21d8b02e844649b2ac54108f4125b85c
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06358995B1

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