Hydrochloric Acid → (3-Bromo-2-fluorophenyl)(trimethyl)silane

HRID 2358129Notes

Reaction equation

HRID 2358129 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[F:8].[CH3:9][Si:10](Cl)([CH3:12])[CH3:11].C([N-]C(C)C)(C)C.[Li+].Cl>O1CCCC1>[CH3:9][Si:10]([CH3:12])([CH3:11])[C:4]1[C:3]([F:8])=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 612591-Bromo-2-fluorobenzeneHCID 2724682Lithium diisopropylamide

Product 1

HCID 14937357(3-Bromo-2-fluorophenyl)(trimethyl)silaneYield 81.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-bromo-2-fluorobenzene (2.0 g, 11.42 mmol) and trimethylsilyl chloride (5.79 ml, 45.69 mmol) in dry tetrahydrofurane (30 ml) at −78° C., under nitrogen, lithium diisopropylamide (2 M in hexane, 28 ml, 12.56 mmol) was added dropwise. The mixture was stirred for 1 h and then brought to ambient temperature. 10% Hydrochloric acid (100 ml) was added and the mixture was extracted with ethyl acetate (3×100 ml). The combined organic phases was dried (MgSO4), filtered and evaporated to dryness. The oily residue was purified by flash column chromatography (ethyl acetate/isooctane, 1:1) to give the title compound (2.3 g). MS m/z (rel. intensity, 70 eV) 248 (M+, 22), 246 (20), 151 (96), 105 (bp), 75 (64).

Workup

  1. custombrought to ambient temperature
  2. extractionthe mixture was extracted with ethyl acetate (3×100 ml)
  3. dry with materialThe combined organic phases was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe oily residue was purified by flash column chromatography (ethyl acetate/isooctane, 1:1)

Sources & evidence

ORD record
ord-9f354548c90d4cd5bbb4666faf9fb182
Source dataset
uspto-grants-2010_07
Patent number
US07763639B2

Reaction notes

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