Allyl bromide → HCID 69119699, compound

HRID 2118334Notes

Reaction equation

HRID 2118334 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=1)(=[O:4])=[O:3].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:22](Br)[CH:23]=[CH2:24].[CH2:26]1[CH2:30]OC[CH2:27]1>>[CH2:22]([CH:1]([S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=1)(=[O:4])=[O:3])[CH2:30][CH:26]=[CH2:27])[CH:23]=[CH2:24]

Participants

5

Reactant 4

HCID 7841Allyl bromideHCID 8028Tetrahydrofuran2×HCID 2733832Lithium HexamethyldisilazideHCID 2757146Benzene, 1-bromo-3-(methylsulfonyl)-

Product 1

HCID 69119699HCID 69119699, compound

Procedure

To a stirred solution of 3-bromophenyl methyl sulfone (Tet. Left. 1994, 35, 9063; 4.74 g) in THF (200 ml) at −78° under nitrogen was added a solution of lithium bis(trimethylsilyl)amide (19 ml, 1.06M in THF) dropwise. The mixture was stirred for 25 min before a solution of allyl bromide (2.44 g) in THF (10 ml) was added. The mixture was allowed to stir at −78° for 1.5 h then quenched with an aqueous solution of ammonium chloride. The product was extracted with EtOAc, and the organic phase washed with brine, dried (MgSO4) and evaporated to dryness. The residual oil was purified on a silica SPE bond elut cartridge (100 g) using a gradient of 5%-40% diethyl ether in cyclohexane (Gradmaster™). The appropriate fractions were evaporated to give the title compound (1.66 g) LCMS RT=3.40 min.

Workup

  1. additionwas added
  2. customthen quenched with an aqueous solution of ammonium chloride
  3. extractionThe product was extracted with EtOAc
  4. washthe organic phase washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness
  7. customThe residual oil was purified on a silica SPE bond elut cartridge (100 g)
  8. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-88b17bf9ab8640b79cf012abd591206c
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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