Phosphorus tribromide → HCID 57429660, compound

HRID 889022Notes

Reaction equation

HRID 889022 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:9]2[CH2:11][CH:10]2[CH2:12]O)[CH:6]=[CH:7][CH:8]=1.[Br:16]P(Br)Br>C(OCC)C>[Br:16][CH2:12][CH:10]1[CH2:11][CH:9]1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:15])([F:14])[F:1])[CH:4]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 53275778HCID 53275778, compound

Product 1

HCID 57429660HCID 57429660, compoundYield 145.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

[2-(3-Trifluoromethyl-phenyl)-cyclopropyl]-methanol obtained in step 1 (0.250 g, 1.15 mmol) was taken in diethyl ether (4 ml) and cooled to 0° C. Tribromo phosphine (0.06 ml, 0.64 mmol) in diethyl ether (4 ml) was added slowly at 0° C. and stirred at 15-20° C. for 2 hrs. Reaction mixture was quenched with saturated NaHCO3 solution (20 ml) and extracted with diethyl ether. Organic layer was washed with saturated brine solution, dried over Na2SO4, and evaporated under vacuum to get 1-(2-bromomethyl-cyclopropyl)-3-trifluoromethyl-benzene (0.26 g, 80%) as a sticky mass.

Workup

  1. customReaction mixture
  2. customwas quenched with saturated NaHCO3 solution (20 ml)
  3. extractionextracted with diethyl ether
  4. washOrganic layer was washed with saturated brine solution
  5. dry with materialdried over Na2SO4
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-2bb57fc029c84df882d974ec945325de
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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