Triethylamine → 2-Bromo-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]naphthalene

HRID 654574Notes

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.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH:8]=2)[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-bromo-2-naphthol (3.00 g, 13.5 mmol) in 67 ml of methylene chloride were added 4-dimethylaminopyridine (0.164 g, 1.34 mmol) and t-butyldimethylsilyl chloride (2.64 g, 17.5 mmol). The solution was cooled to 0° C. and triethylamine (2.60 ml, 18.7 mmol) was added. After 1.5 hours the reaction mixture was diluted with ethyl acetate and washed successively with saturated NH4Cl, H2O, and brine. Drying (MgSO4), evaporation, and purification by flash chromatography through 130 g of silica gel (1:4 CH2Cl2 /hexane) yielded 3.83 g (85%) of the title compound.

Workup

washwashed successively with saturated NH4Cl, H2O, and brine
customDrying
custom(MgSO4), evaporation, and purification by flash chromatography through 130 g of silica gel (1:4 CH2Cl2 /hexane)

Sources & evidence

ORD record: ord-7a5010fe382b42748dca95c0d71a32ab
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05132422

Reaction notes

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