Bromine → HCID 69684695, compound

HRID 2085601Notes

Reaction equation

HRID 2085601 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C:7]1[C:15]2[O:14][CH2:13][C:12]([CH3:17])([CH3:16])[C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH3:2].[Br:19]Br>C(O)C>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C:7]1[C:15]2[O:14][CH2:13][C:12]([CH3:17])([CH3:16])[C:11]=2[CH:10]=[C:9]([Br:19])[CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 69685014HCID 69685014, compound2×

Product 1

HCID 69684695HCID 69684695, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred, cooled (ice bath) solution of 3-(3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-propionic acid ethyl ester (Intermediate 75, 0.71 g, 2.86 mmol) in ethanol (14 mL) was treated with bromine (0.3 mL, 5.819 mmol) and the reaction mixture was allowed to gradually warm up to room temperature over 1.5 h. The volatiles were then evaporated in vacuo and the residue was dissolved in diethyl ether and washed with water (×1), aqueous sodium thiosulfate solution (×1) and brine (×1), dried over anhydrous sodium sulfate, filtered and evaporated to afford the title compound as an oil (0.875 g, 93%).

Workup

  1. customThe volatiles were then evaporated in vacuo
  2. dissolutionthe residue was dissolved in diethyl ether
  3. washwashed with water (×1), aqueous sodium thiosulfate solution (×1) and brine (×1)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-f7a7f1b69da54be08d022b9f4d0423a9
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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