Morpholine → 3-Bromo-4-morpholinobenzaldehyde

HRID 990424Notes

Reaction equation

HRID 990424 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[CH:5]=[O:6].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C([O-])([O-])=O.[K+].[K+]>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 1736043-Bromo-4-fluorobenzaldehyde

Product 1

HCID 235060203-Bromo-4-morpholinobenzaldehydeYield 58.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

EX-604A) To a pyridine (15 mL) solution of 3-bromo-4-fluorobenzaldehyde (1.0 g, 4.9 mmol) was added morpholine (0.5 mL, 5.7 mmol) and K2CO3 (0.69 g. 5.0 mmol), and the slurry was refluxed for 18 h. The solvent was removed, and the residue was partitioned between ethyl acetate and water. The organic layer was separated, dried (MgSO4) and evaporated to a yellow oil. Purification by flash chromatography on silica gel eluting with 15% ethyl acetate in hexane gave 0.77 g (58%) of the desired 3-bromo-4-(4-morpholinyl)benzaldehyde product as an white solid. 1H NMR (CDCl3) δ3.18 (m, 4H), 3.90 (m, 4H), 7.10 (d, 1H), 7.78 (d, 1H), 8.07 (s, 1H), 9.83 (s, 1H).

Workup

  1. temperaturethe slurry was refluxed for 18 h
  2. customThe solvent was removed
  3. customthe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. customevaporated to a yellow oil
  7. customPurification by flash chromatography on silica gel eluting with 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8bad0787f75e4a0a92abc0592bae04c0
Source dataset
uspto-grants-2002_10
Patent number
US06458803B1

Reaction notes

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