4-Bromo-2-methoxyphenol → HCID 66915305, compound

HRID 449096Notes

Reaction equation

HRID 449096 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH3:10])[CH:3]=1.[CH3:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:16]2[CH:17]=[C:12]([CH3:11])[CH:13]=[CH:14][CH:15]=2)=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

4

Reactant 2

HCID 2622344-Bromo-2-methoxyphenolHCID 27339503-Tolylboronic acid

Product 1

HCID 66915305HCID 66915305, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromo-2-methoxyphenol (1.0 g, 0.0049 mol), 3-methylbenzeneboronic acid (1.7 g, 0.012 mol), TEA (4.1 mL, 0.030 mol), cupric acetate (1.4 g, 0.0079 mol) and DCM (50 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=2.31 (s, 3H), 3.83 (s, 3H), 6.68-6.77 (m, 2H), 6.82 (d, J=8.34 Hz, 1H), 6.87 (d, J=7.58 Hz, 1H), 7.03 (dd, J=8.46, 2.15 Hz, 1H), 7.11 (d, J=2.27 Hz, 1H), 7.17 (t, J=7.83 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-0fcdcfd3f81a4a6fb6901f57d8e0fd8c
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

Loading…