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

HRID 1925244Notes

Reaction equation

HRID 1925244 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-daa60531c2344fb39691cc2cd7b9cc5f
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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