Boron tribromide → HCID 67081467, compound

HRID 1188746Notes

Reaction equation

HRID 1188746 reaction equation
B(Br)(Br)Br.[I:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]3[CH:20]=[C:19]([O:21]C)[CH:18]=[CH:17][C:15]=3[N:16]=2)=[CH:8][CH:7]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[I:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[S:13][C:14]3[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:15]=3[N:16]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 67081740HCID 67081740, compound

Product 1

HCID 67081467HCID 67081467, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1 M in CH2Cl2, 6 mL) was added to an anhydrous CH2Cl2 (20 mL) solution of 4 (550 mg, 1.5 mmol). After stirring at room temperature for 24 h, the reaction mixture was quenched with ice water (10 mL) and neutralized with solid NaHCO3 (1.51 g, 18.0 mmol). The mixture was diluted with pH 7 buffer solution (Fisher, 20 mL) and extracted with dichloromethane-methanol (4:1, 3×100 mL). The extracts were combined, dried with anhydrous Na2SO4, and evaporated. The residue was treated with CH2Cl2/MeOH, to give pure 2-(4-iodophenyl)-1,3-benzothiazol-6-ol (5) as a white solid (295 mg, 55.8%).

Workup

  1. customthe reaction mixture was quenched with ice water (10 mL)
  2. extractionextracted with dichloromethane-methanol (4:1, 3×100 mL)
  3. dry with materialdried with anhydrous Na2SO4
  4. customevaporated
  5. additionThe residue was treated with CH2Cl2/MeOH

Sources & evidence

ORD record
ord-3e2288c7e9294c48b27b8db8561f7ea9
Source dataset
uspto-grants-2014_03
Patent number
US08674101B2

Reaction notes

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