Bromide ion → HCID 58424695, compound

HRID 1408813Notes

Reaction equation

HRID 1408813 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][C:5]2=[O:18].[Br-].[CH2:20]1COC[CH2:21]1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][C:5]2([CH:20]=[CH2:21])[OH:18]

Participants

4

Reactant 3

HCID 259Bromide ionHCID 8028Tetrahydrofuran2×HCID 52705456-Bromoflavanone

Product 1

HCID 58424695HCID 58424695, compound

Procedure

To a solution of 6-bromo-2-phenylchroman-4-one (2.021 g, 6.67 mmol) in anhydrous THF (35 mL) at −78° C. is added a solution of vinylmagnesiun bromide in THF (1 M, 10 mL, 10 mmol) dropwise within 30 min. The reaction temperature is allowed to warm to rt and stirred for another 2 h. The reaction is chilled to 0° C. and quenched with sat. aq. NH4Cl and extracted with ethyl acetate (2×40 mL). The combined organic phases are washed with H2O, brine, and dried over Na2SO4, and filtered. The filtrate is concentrated and the residue is purified through flash chromatography on silica gel to afford 6-bromo-2-phenyl-4-vinylchroman-4-ol as an oil (1.961 g. 89%). MS ESI+ve m/z 313 (M+H—H2O)+.

Workup

  1. temperatureThe reaction is chilled to 0° C.
  2. customquenched with sat. aq. NH4Cl
  3. extractionextracted with ethyl acetate (2×40 mL)
  4. washThe combined organic phases are washed with H2O, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated
  8. customthe residue is purified through flash chromatography on silica gel

Sources & evidence

ORD record
ord-fee191639ad94c8e8386e64921d1cd2a
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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