Hydrogen Bromide → HCID 58999614, compound

HRID 1593612Notes

Reaction equation

HRID 1593612 reaction equation
[CH:1]12[O:7][CH:6]1[CH2:5][CH2:4][CH:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:2]2.[BrH:13].C([O-])(O)=O.[Na+].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.C1(C)C=CC=CC=1.O>[Br:13][CH:6]1[CH2:5][CH2:4][CH:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:2][CH:1]1[OH:7]

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 15691705Ethyl 7-oxabicyclo[4.1.0]heptane-3-carboxylate

Product 1

HCID 58999614HCID 58999614, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 7-oxabicyclo[4.1.0]heptane-3-carboxylate (17.8 g) in CH2Cl2 (350 mL) was added 40% HBr solution (120 mL). The biphasic mixture was stirred vigorously for 25 min, then was neutralized with aqueous NaHCO3 solution. The organic layer was collected and dried over MgSO4, then was concentrated in vacuo. The residue was diluted with toluene (120 mL), and para-toluene sulfonic acid (120 mg, 0.6 mmol) was added. The mixture was heated at 128° C. with azeotropic removal of water over 3.5 hours, then was concentrated in vacuo to afford 21 g of a brown residue, which was used in the next reaction without purification.

Workup

  1. customThe organic layer was collected
  2. dry with materialdried over MgSO4
  3. concentrationwas concentrated in vacuo
  4. additionwas added
  5. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-8fc63e33d83649ca86448ba55bbb2949
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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