Phosphorus tribromide → 3-Cyclobutylbenzyl bromide

HRID 429906Notes

Reaction equation

HRID 429906 reaction equation
[CH:1]1([C:5]2[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=2)[CH2:8]O)[CH2:4][CH2:3][CH2:2]1.P(Br)(Br)[Br:14]>C(Cl)Cl>[CH:1]1([C:5]2[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=2)[CH2:8][Br:14])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 540005133-Cyclobutylbenzyl alcohol

Product 1

HCID 183524913-Cyclobutylbenzyl bromideYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to example 17, 1.29 g of 3-cyclobutylbenzyl alcohol was treated with 0.26 mL of PBr3 in 15 mL of anhydrous CH2Cl2 to afford 1.69 g of crude product (92% pure by 1H-NMR). This material was purified by flash chromatography on 65 g of silica gel hexane) to afford 1.59 g (89%) of 3-cyclobutyl benzyl bromide as a clear liquid.

Workup

  1. customto afford 1.69 g of crude product (92% pure by 1H-NMR)
  2. customThis material was purified by flash chromatography on 65 g of silica gel hexane)

Sources & evidence

ORD record
ord-d7c4c3e55617498dbb261ad683546e92
Source dataset
uspto-grants-2001_11
Patent number
US06319702B1

Reaction notes

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