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

HRID 24397

Reaction equation

HRID 24397 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7308f1473c8344e5a43cb77d674dfd60
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Linked notes

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