Dichloromethane → HCID 66915533, compound

HRID 449087Notes

Reaction equation

HRID 449087 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH3:10])[CH:3]=1.[F: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:15]=[CH:14][CH:13]=[C:12]([F:11])[CH:17]=2)=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 2622344-Bromo-2-methoxyphenolHCID 27339863-Fluorophenylboronic acid

Product 1

HCID 66915533HCID 66915533, compound

Procedure

4-Bromo-2-methoxyphenol (1.4 g, 0.0071 mol), 3-fluorobenzeneboronic acid (500 mg, 0.004 mol), TEA (3.0 mL, 0.021 mol), cupric acetate (1.0 g, 0.0057 mol) and DCM (40 mL, 0.6 mol) 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=3.71 (s, 3H), 6.52 (dt, J=10.36, 2.40 Hz, 1H), 6.57-6.69 (m, 2H), 6.81 (d, J=8.34 Hz, 1H), 6.99 (dd, J=8.34, 2.27 Hz, 1H), 7.04 (d, J=2.27 Hz, 1H), 7.13 (td, J=8.34, 6.82 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-312f43fead1849cb998791c8ad0aaf8a
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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