Phenylboronic Acid → 2-Methoxy-4-phenoxybromobenzene

HRID 449092Notes

Reaction equation

HRID 449092 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[O:9][CH3:10].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][C:3]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 66827Phenylboronic AcidHCID 3479554-Bromo-3-methoxyphenol

Product 1

HCID 189257722-Methoxy-4-phenoxybromobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-bromo-3-methoxyphenol (2.0 g, 0.0098 mol), phenylboronic acid (3.0 g, 0.025 mol), TEA (8.2 mL, 0.059 mol), cupric acetate (2.9 g, 0.016 mol) and DCM (100 mL) were added to a 100 mL oven dried flask and the reaction 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. 1H NMR (400 MHz, CDCl3): δ=3.81 (s, 3H), 6.45 (dd, J=8.72, 2.65 Hz, 1H), 6.61 (d, J=2.53 Hz, 1H), 7.01 (d, J=8.34 Hz, 2H), 7.12 (t, J=7.33 Hz, 1H), 7.34 (t, J=7.96 Hz, 2H), 7.42 (d, J=8.59 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-c967bc63a01f408fa0deb95ffe9befba
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

Loading…