Phenylboronic Acid → HCID 21454544, compound

HRID 449093Notes

Reaction equation

HRID 449093 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[Cl: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[Cl:9]

Participants

4

Reactant 2

HCID 66827Phenylboronic AcidHCID 70181824-Bromo-3-chlorophenol

Product 1

HCID 21454544HCID 21454544, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-bromo-3-chlorophenol (2.0 g, 0.0096 mol), phenylboronic acid (3.5 g, 0.029 mol), TEA (8.1 mL, 0.058 mol), cupric acetate (3.2 g, 0.017 mol) and DCM (40 mL) were added to a 100 mL oven dried flask and the reaction was stirred at rt for 24 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=6.74 (dd, J=8.84, 2.78 Hz, 1H), 6.94-7.02 (m, 2H), 7.06 (d, J=2.78 Hz, 1H), 7.14 (t, J=7.33 Hz, 1H), 7.29-7.38 (m, 2H), 7.48 (d, J=8.84 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-850f2004bf4f4f708509ddf3f698e6ff
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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