Dichloromethane → HCID 59570036, compound

HRID 2071124Notes

Reaction equation

HRID 2071124 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH:16]([B-](F)(F)F)=[CH2:17].[K+].C(Cl)Cl.CCN(CC)CC>CC(O)C.O.CCOC(C)=O>[CH:16]([C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])=[CH2:17]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 1039541,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl esterHCID 23679353Potassium vinyltrifluoroborate

Product 1

HCID 59570036HCID 59570036, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of dimethyl 5-bromoisophthalate (273 mg, 1.0 mmol), potassium vinyltrifluoroborate (134 mg, 1.0 mmol) PdCl2(dppf).CH2Cl2 (16.3 mg, 0.02 mmol) and Et3N (0.42 mL, 3.0 mmol) in i-PrOH (6 mL) and H2O (3 mL) was heated to reflux for 3 h. The solution was cooled to room temperature and diluted with EtOAc and H2O. The layers were separated and the aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layer was washed with brine, dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (8% EtOAc in hexanes) to provide dimethyl 5-vinylisophthalate (153.6 mg, 70%).

Workup

  1. temperatureto reflux for 3 h
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (2×10 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (8% EtOAc in hexanes)

Sources & evidence

ORD record
ord-fc5cbc2b87294ba8978e4ee5503ce454
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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