Methyl iodide → HCID 58424290, compound

HRID 1408807Notes

Reaction equation

HRID 1408807 reaction equation
[Li][CH2:2]CCC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CI.[Br:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[O:34][CH:33]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:32][C:31]2=O>C1COCC1>[Br:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[O:34][CH:33]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:32][C:31]2=[CH2:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11776TriphenylphosphineHCID 52705456-BromoflavanoneHCID 178418339Butyllithium

Product 1

HCID 58424290HCID 58424290, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of n-BuLi (2.5 M, 3.80 mL) was added to a mixture of PPh3.MeI. (4.092 g, 10.13 mmol) in THF at −10. The mixture was stirred for 1 h at the same temperature, and then 6-bromo-2-phenylchroman-4-one (2 g, 6.62 mmol) was added. The mixture was allowed to warm to room temperature and stirred for 3 h. The resulting mixture was concentrated and purified by column chromatography to give 6-bromo-4-methylene-2-phenylchroman (400 mg, 20%). 1H-NMR (CDCl3): 2.76 (m, 2H), 4.90 (d, 1H), 5.01 (m, 1H), 5.48 (d, 1H), 6.76 (d, 1H), 7.31 (m, 6H), 7.62 (d, 1H).

Workup

  1. stirringstirred for 3 h
  2. concentrationThe resulting mixture was concentrated
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-76f292bda5a34ddeb144333710a8ec66
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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