Carbon tetrabromide → HCID 20482698, compound

HRID 2387659Notes

Reaction equation

HRID 2387659 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:11]O)[CH:8]=[CH:9][CH:10]=1)[CH:2]=[CH2:3].C(Br)(Br)(Br)[Br:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][Br:14])[CH:6]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 28065595{3-[(Prop-2-en-1-yl)oxy]phenyl}methanol

Product 1

HCID 20482698HCID 20482698, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

To a solution of (3-allyloxy-phenyl)-methanol (Tetrahedron, 2000, 56(13), 1873-1882) (1.07 g, 6.49 mmol) in THF (7 mls) at 3° C. was added carbon tetrabromide (2.69 g, 8.11 mmol) then triphenylphosphine (2.13 g, 8.11 mmol) in THF (2 mls). The reaction mixture was stirred at 5° C. for 1 hour. The reaction mixture was filtered and concentrated in vacuo. The residue was washed with pentane to give a yellow solid which was purified by column chromatography on silica gel, eluting with pentane:ethyl acetate, 100:0, to 95:5 to afford the title compound as a pale yellow oil in 24% yield, 350 mg.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. washThe residue was washed with pentane
  4. customto give a yellow solid which
  5. customwas purified by column chromatography on silica gel
  6. washeluting with pentane

Sources & evidence

ORD record
ord-1c8d61c1235546bbb3432c0aa0819e1d
Source dataset
uspto-grants-2012_09
Patent number
US08268881B2

Reaction notes

Loading…