Boron tribromide → HCID 14424740, compound

HRID 1165479Notes

Reaction equation

HRID 1165479 reaction equation
C[O:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 14424739HCID 14424739, compound2×

Product 1

HCID 14424740HCID 14424740, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The 4-methoxy-2-(4-methoxyphenyl)benzothiazole (9.0 g) obtained in (2) was dissolved in 15 ml of dichloromethane, and a solution of 8.7 g of boron tribromide in 15 ml of dichloromethane was added dropwise to the solution. The mixture was stirred at room temperature for 2 hours, and then poured into 200 ml of ice water, followed by extraction with chloroform three times. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography (eluted with chloroform) to give 4.2 g of 4-hydroxy-2-(4-methoxyphenyl)benzothiazole.

Workup

  1. extractionfollowed by extraction with chloroform three times
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. washThe residue was subjected to silica gel column chromatography (eluted with chloroform)

Sources & evidence

ORD record
ord-106d829cad2d4cd49efa341ec55b82b3
Source dataset
uspto-grants-1990_03
Patent number
US04910211

Reaction notes

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