Oxygen → HCID 66915608, compound

HRID 449104Notes

Reaction equation

HRID 449104 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=1B(O)O.O=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:11]2[C:10]([F:9])=[CH:15][CH:14]=[CH:13][C:12]=2[F:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 977OxygenHCID 78084-BromophenolHCID 27343362,6-Difluorophenylboronic acid

Product 1

HCID 66915608HCID 66915608, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 100 mL round bottom flask was added 4-bromophenol (2.19 g, 12.7 mmol), 2,6-difluorophenylboronic acid (1.00 g, 6.33 mmol), cupric acetate (1.4 g, 7.70 mmol) and DCM (50 mL). TEA (4.0 mL, 29.0 mmol) was then added followed by 4 A° molecular sieves and the reaction mixture was stirred at rt for 48 h with an air balloon to supply oxygen. Purification by flash column chromatography using 5% EtOAc in hexanes afforded the title compound as a colorless oil.

Workup

  1. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-67c2e0b300df4050907c421b38b505f8
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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