Acetic Anhydride → HCID 59736724, compound

HRID 252867Notes

Reaction equation

HRID 252867 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>>[C:12]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[N+:9]([O-:11])=[O:10])(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 243644-Bromo-2-nitrophenol

Product 1

HCID 59736724HCID 59736724, compoundYield 87%

Procedure

A solution of 4-bromo-2-nitrophenol (297, 1.00 g, 4.59 mmol) (scheme 65) in acetic anhydride (10 mL) was heated in a pressure vessel at 130-140° C. for 16 h. Most of the solvent was evaporated in vacuo and the resulting oil was kept in the freezer for 3 days. Crystallization occurred while thawing. The white crystals were suspended in a mixture of EtOAc/hexanes (9:1) and collected by filtration affording the title compound 328 (1.03 g, 87% yield). 1H NMR: (400 MHz, DMSO-d6) δ (ppm): 8.33 (d, J=2.3 Hz, 1H), 8.02 (dd, J=8.6, 2.3 Hz, 1H), 7.45 (d, J=8.6 Hz, 1H), 2.33 (s, 3H). LRMS: (m/z): 282.0/284.0 ((M+/M+2)+23).

Workup

  1. customMost of the solvent was evaporated in vacuo
  2. customCrystallization
  3. additionThe white crystals were suspended in a mixture of EtOAc/hexanes (9:1)
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-bac97a7c7c0c4f2cbef7aebe9bf2286a
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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