Acetic Acid → HCID 21914401, compound

HRID 2410914Notes

Reaction equation

HRID 2410914 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([Cl:10])[CH:3]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CCOC(C)=O.C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[C:4]([Cl:10])[CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 141091094-Bromo-2-chlorobenzaldehyde

Product 1

HCID 21914401HCID 21914401, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Bromo-2-chlorobenzaldehyde (1 g, 4.56 mmol), morpholine (0.457 mL, 5.24 mmol), acetic acid (0.300 mL, 5.24 mmol) and sodium triacetoxyborohydride (1.45 g, 6.84 mmol) were mixed with THF (4 mL) in a sealed microwave vial. The mixture was stirred at r.t. for 2 hrs. The mixture was diluted with EtOAc, washed with H2O. The organic layer was washed with brine, dried over MgSO4 and concentrated. The crude was purified on BIOTAGE® with 0-20% of EtOAc in hexane. The fractions containing the desired product was collected and concentrated to give 1.01 g titled product. MS (ESI) m/z 289.9 (M+H)+.

Workup

  1. washwashed with H2O
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude was purified on BIOTAGE® with 0-20% of EtOAc in hexane
  6. additionThe fractions containing the desired product
  7. customwas collected
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-81a8cd38a1534a899e8d5139fc1e3d30
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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