Imidazole → (S)-(4-Bromo-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)(tert-butyl)dimethyl-silane

HRID 237609Notes

Reaction equation

HRID 237609 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]2[C:3]=1[CH2:4][CH2:5][C@@H:6]2[OH:12].N1C=CN=C1.[C:18]([Si:22]([CH3:25])([CH3:24])Cl)([CH3:21])([CH3:20])[CH3:19].O>CN(C)C=O>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]2[C:3]=1[CH2:4][CH2:5][C@@H:6]2[O:12][Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 86697104(S)-4-bromo-7-fluoro-2,3-dihydro-1H-inden-1-ol

Product 1

HCID 86697280(S)-(4-Bromo-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)(tert-butyl)dimethyl-silane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-4-bromo-7-fluoro-2,3-dihydro-1H-inden-1-ol (6.8 g) and imidazol (5 g) are dissolved at 0° C. in N,N-dimethylformamide (NMP, 25 mL), treated with tert.-butyldimethylchlorosilane (6.3 g) and stirred for 2 hours at room temperature. Water is added and the mixture is stirred for 10 minutes. Then the mixture is partitioned between 1 M hydrochloric acid and ethyl acetate. The organic phase is dried (MgSO4) and concentrated to give the title compound. Yield: 9.25 g.

Workup

  1. stirringthe mixture is stirred for 10 minutes
  2. customThen the mixture is partitioned between 1 M hydrochloric acid and ethyl acetate
  3. dry with materialThe organic phase is dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-265cebac5c4c40388c96f979e36b018c
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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