1,2-Dichloroethane → 3-(Bromomethyl)[1,4]benzodioxino[2,3-c]pyridazine

HRID 1503209Notes

Reaction equation

HRID 1503209 reaction equation
[N:1]1[C:6]2[O:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[O:10][C:5]=2[CH:4]=[C:3]([CH2:15]O)[N:2]=1.ClCCCl.S(Br)([Br:23])=O>C(Cl)(Cl)Cl>[Br:23][CH2:15][C:3]1[N:2]=[N:1][C:6]2[O:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[O:10][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 68176Thionyl bromideHCID 117691161[1,4]Benzodioxino[2,3-c]pyridazin-3-ylmethanol

Product 1

HCID 1176911713-(Bromomethyl)[1,4]benzodioxino[2,3-c]pyridazineYield 76.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To [1,4]benzodioxino[2,3-c]pyridazin-3-ylmethanol (8.1 g) was added 1,2-dichloroethane (80 ml) and the mixture was stirred. Thionyl bromide (38.9 g) was added, and the mixture was stirred with heating under reflux for 2 hr. The mixture was diluted with chloroform, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure, and the residue was washed with diethyl ether to give 3-(bromomethyl)[1,4]benzodioxino[2,3-c]pyridazine (8.0 g).

Workup

  1. stirringthe mixture was stirred
  2. temperaturewith heating
  3. temperatureunder reflux for 2 hr
  4. washthe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure
  7. washthe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-3f803cb22eaf43f0b58863a65172723a
Source dataset
uspto-grants-2015_12
Patent number
US09212147B2

Reaction notes

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