1,2-Dichloroethane → (4-Bromo-2-fluorophenyl)(morpholino)methanone

HRID 2114386Notes

Reaction equation

HRID 2114386 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([F:11])[CH:3]=1.C(Cl)CCl.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[O:8])=[C:4]([F:11])[CH:3]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 3026814-Bromo-2-fluorobenzoic acid

Product 1

HCID 24705647(4-Bromo-2-fluorophenyl)(morpholino)methanoneYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromo-2-fluorobenzoic acid (5.00 g, 22.8 mmol, 1.00 equiv) and EDC (5.23 g, 27.4 mmol, 1.20 equiv) were dissolved in dichloromethane (100 mL). Morpholine (4.77 mL, 54.8 mmol, 2.40 equiv) was added and the solution was maintained at room temperature for 19 h. The reaction mixture was concentrated en vacuo and diluted with EtOAc and 1N HCl. The phases were separated and the organic phase was washed sequentially with water, saturated NaHCO3, and saturated NaCl. The organic phase was subsequently dried over Na2SO4, filtered and concentrated to afford 5.06 g (81%) of a colorless oil which was used without further purification in the next step. MS (ES) m/e 289 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated en vacuo
  2. additiondiluted with EtOAc and 1N HCl
  3. customThe phases were separated
  4. washthe organic phase was washed sequentially with water, saturated NaHCO3, and saturated NaCl
  5. dry with materialThe organic phase was subsequently dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-16a8d6522c15462bbee44106d4196e43
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

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