Water → HCID 135966585, compound

HRID 1709973Notes

Reaction equation

HRID 1709973 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[C:23]([O:24]C)=[CH:22][C:10]2[S:11][C:12]([C:14]3[CH:15]([CH3:21])[CH2:16][C:17](=[O:20])[NH:18][N:19]=3)=[CH:13][C:9]=2[CH:8]=1.O>ClCCl>[OH:6][C:7]1[C:23]([OH:24])=[CH:22][C:10]2[S:11][C:12]([C:14]3[CH:15]([CH3:21])[CH2:16][C:17](=[O:20])[NH:18][N:19]=3)=[CH:13][C:9]=2[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 131100129425-83-8

Product 1

HCID 135966585HCID 135966585, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1.55 ml) was added to a stirred solution of 4,5-dihydro-6-(5,6-dimethoxy-benzo[b]thien-2-yl)-5-methyl-3(2H)-pyridazinone (1.14 g) in dichloromethane (200 ml). After 2 hours the orange solution was cooled in ice, and water (40 ml) was added. The dichloromethane was then evaporated off under reduced pressure and the residual suspension was filtered to give 4,5-dihydro-6-(5,6-dihydroxy-benzo[b]thien-2-yl)-5-methyl-3(2H)-pyridazinone (0.97 g) as a yellow solid. Crystallisation from dichloromethane:methanol and diethylether gave 4,5-dihydro-6-(5,6-dihydroxybenzo[b]thien-2-yl)-5-methyl-3(2H)-pyridazinone. m.p. >270° C.

Workup

  1. temperatureAfter 2 hours the orange solution was cooled in ice
  2. customThe dichloromethane was then evaporated off under reduced pressure
  3. filtrationthe residual suspension was filtered

Sources & evidence

ORD record
ord-c6d0e31000164bceaabc0c91fff603de
Source dataset
uspto-grants-1990_08
Patent number
US04952571

Reaction notes

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