Hydrogen Bromide → HCID 54525055, compound

HRID 1169189Notes

Reaction equation

HRID 1169189 reaction equation
[CH:1]1([CH:6]2[CH2:10][O:9][C:8](=O)[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[BrH:12].[CH3:13][CH2:14][OH:15]>O>[CH2:14]([O:15][C:8](=[O:9])[CH2:7][CH:6]([CH2:10][Br:12])[CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:13]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 702EthanolHCID 12664736HCID 12664736, compound

Product 1

HCID 54525055HCID 54525055, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Preparation of 3-bromomethyl-3-cyclopentyl-propionic acid ethyl ester—A solution of 4-cyclopentyl-dihydro-furan-2-one (4.4 g, 28.5 mmol) in 100 mL of EtOH is saturated with HBr at 0° C. The mixture is warmed to room temperature overnight. It is diluted with 200 mL of H2O and extracted with Et2O (3,100 mL). The combined extracts are washed with brine (2.50 mL) and dried over MgSO4. Evaporation of Et2O gives 6.4 g (85% yield) of 3-bromomethyl-3-cyclopentyl-propionic acid ethyl ester as a clear oil. NMR (1H, 400 MHz, CDCl3) δ1.1 (2H, m); 1.2 (3H, t); 1.5 (4H, m); 1.8 (3H, m); 1.9 (1H, m); 2.4 (2H, dd); 3.5 (2H, dd); 4.1 (2H,q).

Workup

  1. extractionextracted with Et2O (3,100 mL)
  2. washThe combined extracts are washed with brine (2.50 mL)
  3. dry with materialdried over MgSO4
  4. customEvaporation of Et2O

Sources & evidence

ORD record
ord-f1e7977ea59d4733b8e9bc2ca0d4cf0f
Source dataset
uspto-grants-2003_09
Patent number
US06627771B1

Reaction notes

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