Water → 5-Bromo-2-octylcoumaran

HRID 3063Notes

Reaction equation

HRID 3063 reaction equation
[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[O:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C([O-])(O)=O.[Na+].O.[Br:24]Br>ClCCl>[Br:24][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[O:10][CH:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:17]2

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 516892Sodium BicarbonateHCID 189343122-Octylcoumaran

Product 1

HCID 189343225-Bromo-2-octylcoumaranYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 50 ml-three-necked flask, 2.00 g (8.61 mM) of 2-octylcoumaran and 3.2 ml of dichloremethane were placed and mixed to obtain a solution. To the solution, 0.73 (8.69 mM) of NaHCO3 and 3.2 ml of water were added. To the mixture, a solution of 0.44 ml (0.54 mM) of bromine in 1 ml of dichloromethane were added dropwise in 17 minutes under stirring on an ice bath, followed by stirring for 3 hours and 25 minutes at room temperature. After the reaction, the reaction mixture was poured into ice water and subjected to extraction with dichloromethane, followed by two times washing with a common salt aqueous solution and drying with mirabilite. The resultant mixture was concentrated under reduced pressure to obtain 2.58 g of 5-bromo-2-octylcoumaran (Yield: 96.3%).

Workup

  1. additionmixed
  2. customto obtain a solution
  3. stirringby stirring for 3 hours and 25 minutes at room temperature
  4. customAfter the reaction
  5. extractionsubjected to extraction with dichloromethane
  6. washwashing with a common salt aqueous solution
  7. dry with materialdrying with mirabilite
  8. concentrationThe resultant mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0e0dacda86084c48b46139c9f6c1c731
Source dataset
uspto-grants-1998_03
Patent number
US05733476

Reaction notes

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