2-Amino-5-bromobenzoic acid → HCID 178515535, compound

HRID 926554Notes

Reaction equation

HRID 926554 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[F:12][C:13]([F:25])([F:24])[C:14](=O)[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[CH2:16]([C:15]1[C:14]([C:13]([F:12])([F:25])[F:24])=[N:1][C:2]2[C:3]([C:4]=1[OH:6])=[CH:7][C:8]([Br:11])=[CH:9][CH:10]=2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 798582-Amino-5-bromobenzoic acidHCID 1357671,1,1-Trifluoro-4-phenylbutan-2-oneHCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 178515535HCID 178515535, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 2-amino-5-bromobenzoic acid (2.53 g, 11.7 mmol), 1,1,1-trifluoro-4-phenylbutan-2-one (2.83 g, 14.0 mmol, see reference Yang, D; Wong, M; Yan, Z. J. Org. Chem. 2000, 65, 4179-4184), and Eaton's reagent (8.8 mL) in a sealed pressure tube was heated at 100° C. for 4 hours. The mixture was then cooled down to room temperature, ice-water was added slowly, and the mixture was stirred vigorously for about 15 minutes. The precipitated solid was filtered, washed with water, and air dried over night to afford the title compound as a light brown solid.

Workup

  1. temperatureThe mixture was then cooled down to room temperature
  2. filtrationThe precipitated solid was filtered
  3. washwashed with water, and air
  4. customdried over night

Sources & evidence

ORD record
ord-68c8877ffe5145f0a955173b655ce820
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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