Boron tribromide → HCID 22728130, compound

HRID 2086160Notes

Reaction equation

HRID 2086160 reaction equation
[CH:1]1([NH:5][S:6]([C:9]2[CH:14]=[C:13]([O:15][C:16]3[C:21]([Cl:22])=[CH:20][C:19]([N+:23]([O-:25])=[O:24])=[CH:18][C:17]=3[Cl:26])[CH:12]=[CH:11][C:10]=2[O:27]C)(=[O:8])=[O:7])[CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br>C(Cl)Cl>[CH:1]1([NH:5][S:6]([C:9]2[CH:14]=[C:13]([O:15][C:16]3[C:17]([Cl:26])=[CH:18][C:19]([N+:23]([O-:25])=[O:24])=[CH:20][C:21]=3[Cl:22])[CH:12]=[CH:11][C:10]=2[OH:27])(=[O:7])=[O:8])[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22728152HCID 22728152, compound

Product 1

HCID 22728130HCID 22728130, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-Cyclobutyl-5-(2,6-dichloro-4-nitro-phenoxy)-2-methoxy-benzenesulfonamide (451 mg, 1.0 mmol) in methylene chloride (9 mL) at 0° C. was added boron tribromide (1M in methylene chloride, 2.0 mL, 2.0 mmol), and the mixture was stirred at room temperature for 2 hours. The reaction was quenched with water (25 mL) and stirred at room temperature for 1 hour, then extracted with ethyl acetate (3 times 40 mL). The combined organic extracts were washed with brine (15 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography (5% ethyl acetate in CH2Cl2) to afford the title compound (403 mg). 1H NMR (400 MHz, CDCl3) δ8.39 (s, 1H), 8.28 (s, 2H), 7.05-6.94 (m, 3H), 4.77 (d, 1H), 3.77-3.71 (m, 1H), 2.14-2.07 (m, 2H), 1.75-1.56 (m, 4H). MS (APCI−) Calc: 432.1, Found: 431.2 (M−1).

Workup

  1. customThe reaction was quenched with water (25 mL)
  2. stirringstirred at room temperature for 1 hour
  3. extractionextracted with ethyl acetate (3 times 40 mL)
  4. washThe combined organic extracts were washed with brine (15 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (5% ethyl acetate in CH2Cl2)

Sources & evidence

ORD record
ord-5a0f96d370bf4666b1b525852c6ddf07
Source dataset
uspto-grants-2004_04
Patent number
US06723744B2

Reaction notes

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