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

HRID 963431Notes

Reaction equation

HRID 963431 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.N1C=CN=C1.[C:18]([Si:22]([CH3:25])([CH3:24])Cl)([CH3:21])([CH3:20])[CH3:19].CCOCC>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:25])[CH3:24])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 271446-Bromo-2-naphthalenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 134730832-Bromo-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]naphthaleneYield 99.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 g of 6-bromo-2-naphthol, 13.4 g of imidazole and 15 g of t-butyldimethylchlorosilane were stirred at room temperature in 75 ml of dimethylformamide for 18 hrs. Thereafter, 500 ml of ether were added thereto and the organic phase was washed 5 times with 100 ml of water each time. The organic phases were concentrated and the residue was dried in a high vacuum. 15.0 g of 6-bromo-2-t-butyl-dimethylsilyloxy-naphthaline were isolated as a yellowish solid. Yield: 99%. Mass spectrum (ISP): peaks inter alia at m/e: 338 and 336 (M+, in each case 34%), 281 (100%), 279 (98%), 200 (98%).

Workup

  1. washthe organic phase was washed 5 times with 100 ml of water each time
  2. concentrationThe organic phases were concentrated
  3. customthe residue was dried in a high vacuum

Sources & evidence

ORD record
ord-a8d74481ef374537b9fa2ba3bcba8123
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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