Acetic Anhydride → 2-(Acetylamino)-3-(3-bromo-4-fluorophenyl)-2-propenoic acid

HRID 2265287Notes

Reaction equation

HRID 2265287 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.[C:11]([NH:14][CH2:15][C:16]([OH:18])=[O:17])(=[O:13])[CH3:12].CC([O-])=O.[Na+].CC(OC(C)=O)=O>>[C:11]([NH:14][C:15](=[CH:5][C:4]1[CH:7]=[CH:8][C:9]([F:10])=[C:2]([Br:1])[CH:3]=1)[C:16]([OH:18])=[O:17])(=[O:13])[CH3:12]

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 10972AcetylglycineHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 517045Sodium Acetate

Product 1

HCID 687738442-(Acetylamino)-3-(3-bromo-4-fluorophenyl)-2-propenoic acidYield 80.5%

Conditions

Temperature
130 °C

Procedure

A mixture of 3-bromo-4-fluorobenzaldehyde (50.0 g, 0.25 mol), N-acetylglycine (26.2 g, 0.22 mol), NaOAc (13.8 g, 0.56 mol), and Ac2O (52 mL) was heated at 130° C. for 10 h in a flask fitted with a reflux condenser. The resulting precipitate was collected by filtration, washed with water, and suspended in AcOH (250 mL). This mixture was heated at 100° C. for 1 h in a flask fitted with a reflux condenser, and then was cooled to 0° C. The solids were collected by filtration, washing with water, to give the product as a yellow solid (53.5 g, 76%). MS (ESI−): mass calcd. for C11H9BrFNO3, 301.0; m/z found, 299.9 [M−H]−. 1H NMR (400 MHz, DMSO-d6): 12.80 (br s, 1H), 9.52 (br s, 1H), 7.93 (dd, J=6.9, 1.9, 1H), 7.66 (ddd, J=8.4, 4.8, 1.9, 1H), 7.42 (t, J=8.7, 1H), 7.19 (s, 1H), 1.98 (s, 3H).

Workup

  1. customfitted with a reflux condenser
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. temperatureThis mixture was heated at 100° C. for 1 h in a flask
  5. customfitted with a reflux condenser
  6. temperaturewas cooled to 0° C
  7. filtrationThe solids were collected by filtration
  8. washwashing with water

Sources & evidence

ORD record
ord-6525b425ec25403b9fd57fc672a7f504
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

Loading…