Hexafluorophosphate → 6-bromo-2H-chromene

HRID 1357314Notes

Reaction equation

HRID 1357314 reaction equation
[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:6]=1[CH:7]=[CH2:8])C=C.F[P-](F)(F)(F)(F)F>C1(C)C=CC=CC=1>[Br:13][C:10]1[CH:11]=[CH:12][C:5]2[O:4][CH2:1][CH:8]=[CH:7][C:6]=2[CH:9]=1

Participants

4

Reactant 2

HCID 9886HexafluorophosphateHCID 10800000HCID 10800000, compound

Product 1

HCID 102422416-bromo-2H-chromeneYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 2-allyloxy-5-bromostyrene (416 mg) in toluene (20 ml) is added dropwise to a solution of the allenylidene complex (p-cymene)RuCl(PCy3)(═C═C═CPh2)+PF6− (54 mg) in toluene (5 ml) over a period of 1.5 h at 80° C. After stirring at that temperature for another 16 h, the solvent is evaporated and the crude product purified by flash chromatography affording the title compound (341 mg, 93%). 1H NMR (200 MHz, CDCl3): d=7.15 (dd, 1H), 7.04 (d, 1H), 6.62 (d, 1H), 6.31 (dt, 1H), 5.77 (dt, 1H), 4.86 (dd, 2H).

Workup

  1. customthe solvent is evaporated
  2. customthe crude product purified by flash chromatography

Sources & evidence

ORD record
ord-00025ff6098346a2a0c381d00a8143a2
Source dataset
uspto-grants-2003_07
Patent number
US06590048B1

Reaction notes

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