Phenylboronic Acid → 1-Bromo-4-phenoxy-2-(trifluoromethoxy)benzene

HRID 449094Notes

Reaction equation

HRID 449094 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[O:9][C:10]([F:13])([F:12])[F:11].[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][C:3]=1[O:9][C:10]([F:12])([F:11])[F:13]

Participants

4

Reactant 2

HCID 66827Phenylboronic AcidHCID 177507434-Bromo-3-(trifluoromethoxy)phenol

Product 1

HCID 669155441-Bromo-4-phenoxy-2-(trifluoromethoxy)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromo-3-(trifluoromethoxy)phenol (1.0 g, 0.0039 mol), phenylboronic acid (1900 mg, 0.016 mol), TEA (3.2 mL, 0.023 mol), cupric acetate (1.3 g, 0.0070 mol) and DCM (40 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=6.82 (dd, J 8.97, 2.65 Hz, 1H), 7.00 (dd, J=2.78, 1.26 Hz, 1H), 7.02-7.10 (m, 2H), 7.16-7.24 (m, 1H), 7.36-7.45 (m, 2H), 7.55 (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-4957a348b99e44dc803674e7ed4ba959
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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