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

HRID 1699020Notes

Reaction equation

HRID 1699020 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) δ7.11 (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-97cf922f30464ad39ee66a43a31abf42
Source dataset
uspto-grants-2002_02
Patent number
US06344485B1

Reaction notes

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