Triphenylphosphine → 3-Bromo-4-(2-morpholinoethoxy)benzaldehyde

HRID 24397

반응식

HRID 24397 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[OH:29])[CH:24]=[O:25].O[CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[O:36]1[CH2:37][CH2:38][N:33]([CH2:32][CH2:31][O:29][C:28]2[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][C:21]=2[Br:20])[CH2:34][CH2:35]1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 763083-Bromo-4-hydroxybenzaldehydeHCID 5462977Diethyl azodicarboxylate

생성물 1

HCID 231178973-Bromo-4-(2-morpholinoethoxy)benzaldehyde수율 56%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Triphenylphosphine (6.85 g) was added to a solution of 3-bromo-4-hydroxybenzaldehye (5 g) in tetrahydrofuran (40 ml), followed by addition of 2-hydroxyethylmorpholine (3.01 ml) and then the dropwise addition of diethylazodicarboxylate (4.11 ml). After 12 hours, the reaction was concentrated under reduced pressure, poured into 2N hydrochloric acid (200 ml) and extracted with ethyl acetate (2×150 ml). The aqueous layer was basified to pH 9 with solid sodium bicarbonate and extracted with ethyl acetate (2×150 ml). The organic layers were dried over magnesium sulfate and concentrated to afford 4.4 g (56%) of 4-morpholinoethoxy-3-bromobenzaldehyde as a reddish oil.

후처리

  1. concentrationthe reaction was concentrated under reduced pressure
  2. additionpoured into 2N hydrochloric acid (200 ml)
  3. extractionextracted with ethyl acetate (2×150 ml)
  4. extractionextracted with ethyl acetate (2×150 ml)
  5. dry with materialThe organic layers were dried over magnesium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7308f1473c8344e5a43cb77d674dfd60
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855730B2

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