Cyclopentanecarboxylic acid → 1-Bromocyclopentane-1-carboxylic acid

HRID 852748Notes

Reaction equation

HRID 852748 reaction equation
P(Cl)(Cl)Cl.[CH:5]1([C:10]([OH:12])=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6]1.[Br:13]Br>>[Br:13][C:5]1([C:10]([OH:12])=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 3

HCID 18840Cyclopentanecarboxylic acidHCID 24387Phosphorus trichlorideHCID 24408Bromine

Product 1

HCID 134118411-Bromocyclopentane-1-carboxylic acid

Conditions

Temperature
85 °C

Procedure

Phosphorus trichloride (0.54 mL, 6.20 mmol) was added drop-wise to the mixture of cyclopentanecarboxylic acid (14.2 g, 124 mmol) and bromine (7.35 mL, 143 mmol). The mixture was then gradually heated to 85° C. and stirred at this temperature in a sealed vessel for 12 h. After cooling to ambient temperature, the mixture was partitioned between EtOAc and water. The organic portion was separated, washed with water and brine, and conc. in vacuo to give the title compound as a white solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customthe mixture was partitioned between EtOAc and water
  3. customThe organic portion was separated
  4. washwashed with water and brine

Sources & evidence

ORD record
ord-f2955dc300384f63b7949f249fc4cd12
Source dataset
uspto-grants-2007_08
Patent number
US07253196B2

Reaction notes

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