1,2-Dichloroethane → (4-Bromo-3-fluorophenyl)(morpholin-4-yl)methanone

HRID 1907927Notes

Reaction equation

HRID 1907927 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[F:11].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(N1CCOCC1)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[O:8])=[CH:4][C:3]=1[F:11]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 7525EthylmorpholineHCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 27733414-Bromo-3-fluorobenzoic acid

Product 1

HCID 48474115(4-Bromo-3-fluorophenyl)(morpholin-4-yl)methanoneYield 98.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 500 mL flask was charged with 4-bromo-3-fluorobenzoic acid (5.00 g, 22.83 mmol), 100 mL DMF, morpholine (2.4 ml, 27.5 mmol), and 4-Ethylmorpholine (8.6 ml, 67.9 mmol). HOBt (4.32 g, 32.0 mmol) was added followed by EDC (5.25 g, 27.4 mmol) and the reaction allowed to stir at room temperature for 18 hours. The reaction was concentrated and the resulting orange syrup taken up in 100 mL EtOAc and 100 mL water. The organic layer was washed with 100 mL 2N HCl, 100 mL saturated sodium bicarbonate, and 100 mL saturated sodium chloride. The organic was then dried with MgSO4, filtered, and concentrated to give 6.476 g (98%) of a viscous yellow oil. This material was used without further purification.

Workup

  1. concentrationThe reaction was concentrated
  2. washThe organic layer was washed with 100 mL 2N HCl, 100 mL saturated sodium bicarbonate, and 100 mL saturated sodium chloride
  3. dry with materialThe organic was then dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-16a8eed857194b81a67067ac9d48b707
Source dataset
uspto-grants-2013_12
Patent number
US08598169B2

Reaction notes

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