Phenylboronic Acid → 1-Bromo-2-methyl-4-phenoxybenzene

HRID 449086Notes

Reaction equation

HRID 449086 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[CH3:9]

Participants

4

Reactant 2

HCID 66827Phenylboronic AcidHCID 728574-Bromo-m-cresol

Product 1

HCID 128585521-Bromo-2-methyl-4-phenoxybenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 100 mL round bottom flask was added 4-bromo-3-methylphenol (0.90 g, 0.0048 mol), phenylboronic acid (2.4 g, 0.019 mol), cupric acetate (1.4 g, 0.0077 mol) and DCM (49.99 mL). TEA (4.0 mL, 0.029 mol) was then added followed by 4 A° molecular sieves and the reaction mixture was stirred at rt over night. 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. 1H NMR (400 MHz, CDCl3): δ=2.35 (s, 3H), 6.72 (dd, J=8.59, 3.03 Hz, 1H), 6.91 (d, J=2.78 Hz, 1H), 6.98-7.05 (m, 2H), 7.08-7.16 (m, 1H), 7.31-7.38 (m, 2H), 7.46 (d, J=8.59 Hz, 1H).

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-715ff03d613b4b88801f98caea7487ec
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

Loading…