Pyridine → 1-Bromo-2-phenoxy-benzene

HRID 334259Notes

Reaction equation

HRID 334259 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1C=CC=CC=1>ClCCl.CC([O-])=O.CC([O-])=O.[Cu+2]>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 72442-BromophenolHCID 66827Phenylboronic Acid

Product 1

HCID 374831-Bromo-2-phenoxy-benzeneYield 15.1%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

2-Bromophenol (1.22 mL, 11.6 mmol), phenylboronic acid (2.8 g, 23.1 mmol), Cu(OAc)2 (4.2 g, 23.1 mmol) and pyridine (4.66 mL, 57.8 mmol) were dissolved in dichloromethane (100 mL) in a reaction vessel holding 1 g of 4 Å M.S. and stirred at room temperature for 18 hours. After the reaction was completed, the reaction mixture was diluted with dichloromethane and filtered through Celite. The filtrate was extracted with 1 N NaOH and brine, and the organic layer was dried with anhydrous MgSO4 and filtered again. The filtrate was concentrated under reduced pressure) to obtain 436 mg of the target compound (1.75 mmol, 15.1%).

Workup

  1. filtrationfiltered through Celite
  2. extractionThe filtrate was extracted with 1 N NaOH and brine
  3. dry with materialthe organic layer was dried with anhydrous MgSO4
  4. filtrationfiltered again
  5. concentrationThe filtrate was concentrated under reduced pressure)

Sources & evidence

ORD record
ord-90e33a65ef7c4238965ed2a7af2d01d2
Source dataset
uspto-grants-2014_11
Patent number
US08883796B2

Reaction notes

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