Dichloromethane → 1-Bromo-2-fluoro-5-methoxy-4-phenoxybenzene

HRID 449088Notes

Reaction equation

HRID 449088 reaction equation
[Br:1][C:2]1[C:7]([F: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[F:8]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 66827Phenylboronic AcidHCID 265965254-Bromo-5-fluoro-2-methoxyphenol

Product 1

HCID 669155391-Bromo-2-fluoro-5-methoxy-4-phenoxybenzene

Procedure

4-Bromo-5-fluoro-2-methoxyphenol (500 mg, 0.002 mol), phenylboronic acid (0.73 g, 0.0060 mol), TEA (2.0 mL, 0.014 mol), cupric acetate (0.70 g, 0.0038 mol) and DCM (20 mL, 0.4 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=3.83 (s, 3H), 6.73 (d, J=9.09 Hz, 1H), 6.94-7.00 (m, 2H), 7.07-7.15 (m, 2H), 7.34 (dd, J=8.59, 7.58 Hz, 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-6f1412d3db42475399e6d9b6c5dd4b36
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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