HCID 11176970, compound → HCID 11186232, compound

HRID 895246Notes

Reaction equation

HRID 895246 reaction equation
Br[C:2]1[C:3]([OH:22])=[C:4]([Cl:21])[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[CH:7][C:6]=2[Cl:20].C([Li])(C)(C)C>>[Cl:21][C:4]1[C:5]2[C:10](=[CH:9][C:8]([C:12]3[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=3)=[CH:7][C:6]=2[Cl:20])[CH:11]=[CH:2][C:3]=1[OH:22]

Participants

3

Reactant 2

HCID 11176970HCID 11176970, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 11186232HCID 11186232, compound

Procedure

The title compound was prepared by reacting 3-bromo-1,8-dichloro-6-(4-methoxyphenyl)-2-naphthol (0.30 g, 0.754 mmol) with t-butyl lithium (1.75 mL of 1.7N solution, 3.0 mmol) and quenching with water according to the method use to prepare intermediate 84 to yield 0.19 g (79%) of a yellow solid. An analytical sample was further prepared by reverse phase preparative HPLC to yield the title compound as a light yellow solid: mp 132-134° C.; 1H NMR (DMSO-d6): δ 3.82 (3H, s), 7.06 (2H, d, J=8.77 Hz), 7.37 (1H, d, J=8.90 Hz), 7.77 (2H, d, J=8.75 Hz), 7.89-7.93 (2H, m), 8.15 (1H, d, J=1.85 Hz), 10.68 (1H, s); MS (ESI) m/z 317/319/321 (M−H)−.

Workup

  1. customquenching with water according to the method use
  2. customto prepare intermediate 84

Sources & evidence

ORD record
ord-136de5ee326c42bab0eece2407ca4f6b
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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