Chlorosuccinimide → HCID 11289654, compound

HRID 895243Notes

Reaction equation

HRID 895243 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]2.C1C(=O)N([Cl:28])C(=O)C1>C1COCC1>[Cl:28][C:10]1[C:11]2[C:6](=[CH:5][C:4]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=3)=[CH:3][C:2]=2[F:1])[CH:7]=[CH:8][C:9]=1[OH:12]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 11311694HCID 11311694, compound

Product 1

HCID 11289654HCID 11289654, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-fluoro-6-(4-methoxyphenyl)-2-naphthol (0.17 g, 0.63 mmol) and NCS (0.10 g, 0.76 mmol) in THF (20 mL) were stirred under nitrogen at room temperature overnight according to Method C. The solution was concentrated onto Florosil and purified on a silica column (20% ethyl acetate—hexanes) to yield 0.16 g (84%) of the title compound as a yellow solid. An analytical sample was further prepared by preparative reverse phase HPLC to yield a light yellow solid: mp 120-124° C.; 1H NMR (DMSO-d6): δ 3.82 (3H, s), 7.06 (2H, d, J=8.80 Hz), 7.34 (1H, d, J=8.91 Hz), 7.67 (1H, dd, J=1.69 Hz, J=15.48 Hz), 7.78 (2H, d, J=8.78 Hz), 8.01 (1H, d, J=1.54 Hz), 10.62 (1H, s); MS (ESI) m/z 301/303 (M−H)−.

Workup

  1. concentrationThe solution was concentrated onto Florosil
  2. custompurified on a silica column (20% ethyl acetate—hexanes)

Sources & evidence

ORD record
ord-3f878507f10b4e8692fea71d71c53729
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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