6-Bromo-2-naphthalenol → 6-Bromo-1-fluoronaphthalen-2-OL

HRID 2115755Notes

Reaction equation

HRID 2115755 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:23])(=O)=O)=CC=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([F:23])=[C:7]([OH:12])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 271446-Bromo-2-naphthalenolHCID 588007N-Fluorobenzenesulfonimide

Product 1

HCID 112419406-Bromo-1-fluoronaphthalen-2-OL

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromo-naphthalen-2-ol (5 g, 22.4 mmol, Aldrich) in dry DMF (50 mL, Aldrich) was added N-fluorobenzene sulfonimide (21.9 g, 67.2 mmol, Aldrich). The reaction was stirred at RT for 48 h. The volatile portion was removed in vacuo and the residue was purified by silica gel chromatography (CHCl3) to give title compound as a yellow solid. MS (ESI, neg. ion) m/z: 240.0 (M−1). Mass Calc'd for C10H6BrFO: 239.96.

Workup

  1. customThe volatile portion was removed in vacuo
  2. customthe residue was purified by silica gel chromatography (CHCl3)

Sources & evidence

ORD record
ord-afbfc93b68874f709c3c237abd468f85
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

Loading…