Dichloromethane → 1-Bromo-2,3-difluoro-4-phenoxybenzene

HRID 449090Notes

Reaction equation

HRID 449090 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[C:3]=1[F:10].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(Cl)Cl>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([F:9])[C:3]=1[F:10]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 66827Phenylboronic AcidHCID 102199424-Bromo-2,3-difluorophenol

Product 1

HCID 674344071-Bromo-2,3-difluoro-4-phenoxybenzene

Procedure

4-bromo-2,3-difluorophenol (1.0 g, 0.0048 mol), phenylboronic acid (1.4 g, 0.012 mol), TEA (4.0 mL, 0.029 mol), cupric acetate (1.4 g, 0.0076 mol) and DCM (60 mL, 1 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=6.70 (ddd, J=9.22, 7.33, 2.15 Hz, 1H), 6.95-7.02 (m, 2H), 7.15 (t, J=7.45 Hz, 1H), 7.23 (ddd, J=9.16, 6.88, 2.40 Hz, 1H), 7.31-7.38 (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-328fcb90f56947459ab0f610ae7c96eb
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

Loading…