Boron tribromide → N-[2-(2-hydroxy-phenyl)-ethyl]-methanesulfonamide

HRID 1595853

Reaction equation

HRID 1595853 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][NH:15][S:16]([CH3:19])(=[O:18])=[O:17]>C(Cl)Cl>[OH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][NH:15][S:16]([CH3:19])(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 6465664N-[2-(2-methoxyphenyl)ethyl]methanesulfonamide

Product 1

HCID 22246821N-[2-(2-hydroxy-phenyl)-ethyl]-methanesulfonamideYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1.0 M in CH2Cl2, 80.8 mL, 80.8 mmol) was added to a solution of N-[2-(2-methoxy-phenyl)-ethyl]-methanesulfonamide (18.5 g, 80.8 mmol) in CH2Cl2 (200 mL). The reaction was stirred at room temperature for 2 h and was poured onto water (200 mL). The aqueous layer was extracted with CH2Cl2 (2×) and the organic solution was washed with water (1×) and aqueous NaHCO3 (satd, 1×). The organic solution was dried over MgSO4, filtered, and concentrated to afford N-[2-(2-hydroxy-phenyl)-ethyl]-methanesulfonamide (16.8 g). 1H NMR (400 MHz, CDCl3) δ 7.11 (m, 2H), 6.86 (m, 1H), 6.80 (m, 1H), 4.79 (m, 1H), 3.39 (t, 2H), 2.88 (t, 2H), 2.77 (s, 3H).

Workup

  1. additionwas poured onto water (200 mL)
  2. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  3. washthe organic solution was washed with water (1×) and aqueous NaHCO3 (satd, 1×)
  4. dry with materialThe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-197773502e034b689926c767c053c5a5
Source dataset
uspto-grants-2001_09
Patent number
US06288120B1

Linked notes

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