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

HRID 1797773Notes

Reaction equation

HRID 1797773 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([O:19]C)[CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].B(Br)(Br)Br>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

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

Product 1

HCID 108909996-Benzothiazolol, 2-(4-nitrophenyl)-Yield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-(4′-nitrophenyl)-6-methoxy benzothiazole (400 mg, 1.5 mmol) in CH2Cl2 (10 mL) was added BBr3 (1M in CH2Cl2, 10 mL, 10 mmol). The reaction mixture was stirred at room temperature for 24 hr. The reaction was then quenched with water, and extracted with ethyl acetate (3×20 mL). The organic layers were combined and washed with water, dried over MgSO4, and evaporated. The residue was purified by flash chromatography (silica gel, hexanes:ethyl acetate=1:1) to give the product as a yellow solid (210 mg, 55%). 1HNMR (300 MHz, Acetone-d6) δ (ppm): 9.02(s, OH), 8.41(d, J=9.1 Hz, 1H), 8.33(d, J=9.1 Hz, 1H), 7.96(d, J=8.6 Hz, 1H), 7.53(d, J=2.4 Hz, 1H), 7.15(dd, J1=8.6 Hz, J2=2.4 Hz, 1H).

Workup

  1. customThe reaction was then quenched with water
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was purified by flash chromatography (silica gel, hexanes:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-b4095bf5845d4fc096458d871d5d5cb6
Source dataset
uspto-grants-2013_01
Patent number
US08343457B2

Reaction notes

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