2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 86703675, compound

HRID 1849793Notes

Reaction equation

HRID 1849793 reaction equation
[F:1][C:2]1([F:20])[C:8]2([CH2:9][O:10]CC3C=CC(OC)=CC=3)[CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7]2.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.S([O-])([O-])(=O)=O.[Na+].[Na+]>ClCCl.O>[F:1][C:2]1([F:20])[C:8]2([CH2:9][OH:10])[CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7]2

Participants

6

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 24436Sodium SulfateHCID 86703674HCID 86703674, compound

Product 1

HCID 86703675HCID 86703675, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7,7-difluoro-1-((4-methoxybenzyloxy)methyl)- bicyclo[4.1.0]heptane (2.50 g, 8.90 mmol) in dichloromethane (20 mL) and water (3.0 mL) was added DDQ (3.00 g, 13.3 mmol) at 0° C. The reaction mixture was stirred at the same temperature for 3 hour. Water (1.5 mL) was added followed by sodium sulfate (10 g). The resulting suspension was filtered through a short pad of silica gel column with ethyl acetate in hexanes (30%) to afford the title compound as a colorless liquid (0.90 g, 62%).

Workup

  1. filtrationThe resulting suspension was filtered through a short pad of silica gel column with ethyl acetate in hexanes (30%)

Sources & evidence

ORD record
ord-89ed79f4245f492985646d55cb96a01d
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

Loading…