Phosphorus tribromide → methyl 8-(1-bromoethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate

HRID 572728Notes

Reaction equation

HRID 572728 reaction equation
[Br:1]P(Br)Br.O[CH:6]([C:8]1[CH:9]=[C:10]([C:25]([O:27][CH3:28])=[O:26])[CH:11]=[C:12]2[C:17]=1[O:16][C:15]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[CH:14][C:13]2=[O:24])[CH3:7]>C(Cl)Cl>[Br:1][CH:6]([C:8]1[CH:9]=[C:10]([C:25]([O:27][CH3:28])=[O:26])[CH:11]=[C:12]2[C:17]=1[O:16][C:15]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[CH:14][C:13]2=[O:24])[CH3:7]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromide2×HCID 58235013methyl 8-(1-hydroxyethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate

Product 1

HCID 58234984methyl 8-(1-bromoethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylateYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tribromophosphine (1.65 mL, 1.65 mmol) was added to a stirred suspension of methyl 8-(1-hydroxyethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate (500 mg, 1.50 mmol) in DCM (10 mL) in an ice bath under nitrogen. The resulting solution was stirred at room temperature for 24 hrs. The reaction was incomplete and further tribromophosphine (0.300 mL, 0.30 mmol) was added and the reaction mixture stirred for an additional 12 hrs. The solvent was evaporated, the residue was suspended in water and ice and a sodium carbonate solution was carefully added until pH 6. The precipitate was collected by filtration, washed with water then with diethylether and dried to afford methyl 8-(1-bromoethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate (470 mg, 79%) as a dark beige solid. Mass Spectrum: M+H+ 398.

Workup

  1. stirringthe reaction mixture stirred for an additional 12 hrs
  2. customThe solvent was evaporated
  3. additionice and a sodium carbonate solution was carefully added until pH 6
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. dry with materialwith diethylether and dried

Sources & evidence

ORD record
ord-73db4f8bd15743cfbdd24a175b0fd60e
Source dataset
uspto-grants-2015_05
Patent number
US09029374B2

Reaction notes

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