Phenylboronic Acid → HCID 66915584, compound

HRID 449091Notes

Reaction equation

HRID 449091 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([O:10][CH3:11])[CH:3]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:9][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 66827Phenylboronic AcidHCID 6123034-Bromo-2-methoxy-5-methylphenol

Product 1

HCID 66915584HCID 66915584, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromo-2-methoxy-5-methylphenol (500 mg, 0.002 mol), phenylboronic acid (0.70 g, 0.0058 mol), TEA (1.9 mL, 0.014 mol), cupric acetate (0.67 g, 0.0037 mol) and DCM (30 mL) were added to a 100 mL oven dried flask 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. 1H NMR (400 MHz, CDCl3): δ=2.27 (s, 3H), 3.79 (s, 3H), 6.84 (s, 1H), 6.88-6.96 (m, 2H), 7.00-7.08 (m, 1H), 7.15 (s, 1H), 7.23-7.33 (m, 2H).

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-7fe76fb624da439aa78e395fe64471bb
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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