Dichloromethane → 4-Bromo-2-methyl-1-phenoxybenzene

HRID 449105Notes

Reaction equation

HRID 449105 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1C.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:19](Cl)Cl>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([CH3:19])[CH:7]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 66827Phenylboronic AcidHCID 728574-Bromo-m-cresol

Product 1

HCID 227362534-Bromo-2-methyl-1-phenoxybenzene

Procedure

Into a 100 mL round bottom flask was added 4-bromo-3-methylphenol (1.00 g, 5.35 mmol), benzeneboronic acid (1.30 g, 10.7 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. Reaction mixture was then filtered through celite. The filtrate was concentrated in vacuo to give a residue which was purified by silica gel chromatography, eluting with 5% EtOAc in hexane.

Workup

  1. customReaction mixture
  2. filtrationwas then filtered through celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give a residue which
  5. customwas purified by silica gel chromatography
  6. washeluting with 5% EtOAc in hexane

Sources & evidence

ORD record
ord-c394394afcbc4d53aff9fcf6a904e516
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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