Phenol → 5-Phenoxy-2-benzofuran-1(3H)-one

HRID 1480927Notes

Reaction equation

HRID 1480927 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[O:6][CH2:5]2.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC(C)(C(=O)CC(=O)C(C)(C)C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.Cl[Cu]>[O:18]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[O:6][CH2:5]2)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 6031445-Bromophthalide

Product 1

HCID 445585805-Phenoxy-2-benzofuran-1(3H)-oneYield 88.9%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5-bromo-3H-isobenzofuran-1-one (75.9 g, 0.36 mol) (Sigma-Aldrich), phenol (67.1 g, 0.713 mol), CuCl (17.6 g, 0.178 mol), 2,2,6,6-tetramethyl-heptane-3,5-dione (TMHD, 7.33 mL) and cesium carbonate (232.3 g, 0.713 mol) in NMP (200 mL) was heated at 130° C. for 64 h. After cooled, reaction mixture was poured into ice/2M HCl mixture (1 L). The mixture was then refluxed for 1 h. After cooled, the solid was collected, rinsed with water and dried in vacuo to provide the title compound (72.22 g, 0.32 mol). 1H NMR in DMSO-d6, δ in ppm: 7.82 (dd, 1H, J=1.6 Hz, 7.6 Hz), 7.51-7.40 (m, 2H), 7.3-7.1 (m, 5H), 5.31 (s, 2H).

Workup

  1. temperatureAfter cooled
  2. customreaction mixture
  3. temperatureThe mixture was then refluxed for 1 h
  4. temperatureAfter cooled
  5. customthe solid was collected
  6. washrinsed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-e7d83620441441bd93ef7759b5688216
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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