Boron tribromide → HCID 89157678, compound

HRID 1468675Notes

Reaction equation

HRID 1468675 reaction equation
C[O:2][C:3]1[C:11]([CH3:12])=[CH:10][C:6]2[N:7]=[CH:8][S:9][C:5]=2[CH:4]=1.B(Br)(Br)Br>ClCCl>[CH3:12][C:11]1[C:3]([OH:2])=[CH:4][C:5]2[S:9][CH:8]=[N:7][C:6]=2[CH:10]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 19385238HCID 19385238, compound

Product 1

HCID 89157678HCID 89157678, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 6-methoxy-5-methylbenzo[d]thiazole (5B) (160 mg, 0.89 mmol) in dichloromethane (5 mL) was added boron tribromide (1 M in dichlormethane, 1.8 ml) at 0° C. The reaction mixture was stirred at 0° C. for 2 h. The reaction was quenched by adding a saturated NaHCO3 solution, extracted with dichlormethane and trace MeOH. The organic layer was dried over MgSO4, filtered, concentrated and purified by silica gel column (0-100% Ethyl acetate/hexanes). LCMS-ESI+: calc'd for C8H7NOS: 166.0 (M+H+). Found: 166.2 (M+H+).

Workup

  1. customThe reaction was quenched
  2. additionby adding a saturated NaHCO3 solution
  3. extractionextracted with dichlormethane
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel column (0-100% Ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-739748cb74114f97b16710fa59a8a679
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

Loading…