Boron tribromide → 6-Benzothiazolol, 2-(4-nitrophenyl)-

HRID 643645Notes

Reaction equation

HRID 643645 reaction equation
C[O:2][C:3]1[CH:20]=[CH:19][C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=3)[S:9][C:5]=2[CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[N+:16]([C:13]1[CH:12]=[CH:11][C:10]([C:8]2[S:9][C:5]3[CH:4]=[C:3]([OH:2])[CH:20]=[CH:19][C:6]=3[N:7]=2)=[CH:15][CH:14]=1)([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 106608526-Methoxy-2-(4-nitrophenyl) benzothiazole

Product 1

HCID 108909996-Benzothiazolol, 2-(4-nitrophenyl)-Yield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under N2, 23 (10.4 mmol) was dissolved in CH2Cl2 and, at −40° C., BBr3 (31.4 mmol) was slowly added. The mixture was then stirred 24 hours at room temperature. The reaction mixture was quenched with water and extracted with ethyl acetate (×3 100 ml). The organic layers were combined, dried over Na2SO4 and the solvent was removed via a rotary evaporator. The residue was purified by chromatography on silica gel using 7:3 hexane/ethyl acetate as the eluent to yield 1.53 g (53%) of 24 as a yellow solid.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate (×3 100 ml)
  3. dry with materialdried over Na2SO4
  4. customthe solvent was removed via a rotary evaporator
  5. customThe residue was purified by chromatography on silica gel using 7:3 hexane/ethyl acetate as the eluent

Sources & evidence

ORD record
ord-1a5c7141bea347859b6290983a8985d4
Source dataset
uspto-grants-2010_04
Patent number
US07700616B2

Reaction notes

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