6-Bromo-2-naphthalenol → 6-Bromo-1-chloronaphthalen-2-ol

HRID 1830654Notes

Reaction equation

HRID 1830654 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(=O)N([Cl:20])C(=O)C1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([Cl:20])=[C:7]([OH:12])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 271446-Bromo-2-naphthalenolHCID 31398Chlorosuccinimide

Product 1

HCID 220481596-Bromo-1-chloronaphthalen-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by reacting 6-bromo-2-naphthol (3 g, 13.4 mmol) and NCS (2.47 g, 18.5 mmol) in THF (50 mL) according to method C to yield 2.2 g (64%) of yellow solid: 1H NMR (DMDO-d6): δ 7.34 (1H, d, J=8.87 Hz), 7.69 (1H, dd, J=1.75 Hz, J=6.09 Hz), 7.79 (1H, d, J=8.96 Hz), 7.96 (1H, d, J=9.03 Hz), 8.17 (1H, d, J=1.75 Hz), 10.68(1H, s); MS (ESI) m/z 255/257/259 (M−H)−.

Sources & evidence

ORD record
ord-68ea074e115f4179bdc69d7e8dbf816d
Source dataset
uspto-grants-2006_06
Patent number
US07067524B2

Reaction notes

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