6-Bromo-2-naphthalenol → 2,3,5,6-Tetrabromo-4-methylphenol

HRID 895208Notes

Reaction equation

HRID 895208 reaction equation
[N+]([C:4]1([CH3:15])[C:9]([Br:10])=[C:8]([Br:11])[C:7](=[O:12])[C:6]([Br:13])=[C:5]1[Br:14])([O-])=O.BrC1C=C2C(=CC=1)C=C(O)C=C2>CCOCC>[Br:11][C:8]1[C:9]([Br:10])=[C:4]([CH3:15])[C:5]([Br:14])=[C:6]([Br:13])[C:7]=1[OH:12]

Participants

4

Reactant 2

HCID 271446-Bromo-2-naphthalenolHCID 27245472,3,5,6-Tetrabromo-4-methyl-4-nitro-2,5-cyclohexadien-1-one

Product 1

HCID 4581392,3,5,6-Tetrabromo-4-methylphenolYield 6.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Nitro-4-methyl-2,3,5,6-tetrabromo-2,5-cyclohexadien-1-one (2.53 g, 4.95 mmol, purity: 82.6%) was added to 6-bromo-2-naphthol (1 g, 4.5 mmol) in 40 mL of dry ether. The reaction was allowed to react for 1.5 hr at room temperature. The solid was filtered to give 2,3,5,6-tetrabromo-4-methyl-phenol (144 mg). The solution was then evaporated under vacuum. The crude mixture was dissolved in ethyl acetate and washed with water. The organic layer was dried over anhydrous Na2SO4 and filtered and the solvent removed under vacuum. 2,3,5,6-tetrabromo-4-methyl-phenol (1.2 g) was separated by recrystallization of the crude product with ethyl acetate—hexane. The mother liquid was concentrated onto Florosil and purified on a silica column (15%-20% ethyl acetate-hexane) to yield 0.731 g (61%) of the title compound as a yellow solid: mp 111-113° C.; 1H NMR (DMDO-d6): δ 7.39 (1H, d, J=9.07 Hz), 7.54 (1H, d, J=9.05 Hz), 7.75 (1H, dd, J=9.05 Hz, J=1.70 Hz), 8.03 (1H, d, J=9.14 Hz), 8.29 (1H, d, J=1.84 Hz), 11.65 (1H, s); MS (ESI) m/z 266/268 (M−H)−; IR 1350 cm−1, 1490 cm−1.

Workup

  1. customto react for 1.5 hr at room temperature
  2. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-4ca453509559499990391998e6beb97c
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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