Water → 4-(8-hydroxy-2H-chromen-3-ylcarbonyl)morpholine

HRID 460548Notes

Reaction equation

HRID 460548 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[O:11][CH2:10][C:9]([C:13]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])=[CH:8]2.B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[O:11][CH2:10][C:9]([C:13]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])=[CH:8]2

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 107548644-(8-methoxy-2H-chromen-3-ylcarbonyl)morpholine

Product 1

HCID 105633504-(8-hydroxy-2H-chromen-3-ylcarbonyl)morpholineYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (70 ml) of 4-(8-methoxy-2H-chromen-3-ylcarbonyl)morpholine (3.5 g) in methylene chloride was added dropwise boron tribromide (9.5 g) at −78° C. The reaction temperature was set to room temperature and the mixture was stirred for 2 hr. The reaction mixture was poured into water and stirred for 1 hr. The organic layer was separated and washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (3.3 g) as brown crystals.

Workup

  1. customwas set to room temperature
  2. stirringstirred for 1 hr
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-59d077f9f5c044e7af2e0266a3a9785e
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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