Acetic Acid → HCID 22285325, compound

HRID 1874076Notes

Reaction equation

HRID 1874076 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=O.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(O)(=O)C.[Na].C(=O)([O-])O.[Na+]>ClCCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH2:7][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 5360545Sodium

Product 1

HCID 22285325HCID 22285325, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

5-Bromo-2-fluorobenzaldehyde (2.5 g, 12.3 mmol) and morpholine (1.62 g, 18.5 mmol) are dissolved in 50 mL DCE and stirred for 0.5 h. Acetic acid (0.42 mL, 7.4 mmol) and sodium trisacetoxyboronhydride (3.92 g, 18.5 mmol) are added and the reaction mixture is stirred for 2 h. Then 50 mL of a saturated aqueous solution of sodium hydrogencarbonate is added and the reaction mixture is stirred for another 0.5 h. The reaction mixture is extracted with DCM and the combined organic phases are dried over MgSO4 and concentrated in vacuo. Yield: 3.02 g.

Workup

  1. stirringthe reaction mixture is stirred for 2 h
  2. stirringthe reaction mixture is stirred for another 0.5 h
  3. extractionThe reaction mixture is extracted with DCM
  4. dry with materialthe combined organic phases are dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb4bd5b539dd4ef5a71f8432fcd66e98
Source dataset
uspto-grants-2012_11
Patent number
US08304556B2

Reaction notes

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