Chlorosuccinimide → 3-Bromo-8-chloro-7-hydroxy-1-naphthonitrile

HRID 895256Notes

Reaction equation

HRID 895256 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:13]#[N:14])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([OH:12])[CH:6]=2.C1C(=O)N([Cl:22])C(=O)C1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:13]#[N:14])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([OH:12])[C:6]=2[Cl:22]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 113225983-Bromo-7-hydroxy-1-naphthonitrile

Product 1

HCID 114829513-Bromo-8-chloro-7-hydroxy-1-naphthonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by reacting 3-bromo-7-hydroxy-1-naphthonitrile (0.32 g, 1.28 mmol) with NCS (0.24 g, 1.8 mmol) in THF (25 mL) at 45° C. for 3 hr according to method C to yield 0.30 g (83%) of a yellow solid. An analytical sample was prepared by preparative reverse phase HPLC to yield the title compound as a white solid: mp 148-150° C.; 1H NMR (DMSO-d6): δ 7.47 (1H, d, J=8.98 Hz), 7.95 (1H, d, J=9.02 Hz), 8.32 (1H, d, J=2.08 Hz), 8.55 (1H, d, J=2.08 Hz), 11.33 (1H, s); MS (ESI) m/z280/282/284 (M−H)−

Workup

  1. customat 45° C.
  2. customfor 3 hr

Sources & evidence

ORD record
ord-fcc2b242e01e467aa8c367324b1286d6
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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