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

HRID 1084726Notes

Reaction equation

HRID 1084726 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

7

Reactant 3

HCID 8471TriethylamineHCID 271446-Bromo-2-naphthalenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 134730832-Bromo-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]naphthaleneYield 85%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

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

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

Sources & evidence

ORD record
ord-0f8b5565b7524bbfa408d96b54d1f488
Source dataset
uspto-grants-1991_04
Patent number
US05006519

Reaction notes

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