4-Fluoroaniline → HCID 67977427, compound

HRID 467456Notes

Reaction equation

HRID 467456 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(OCC)(=O)C>[F:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]=[CH:22][C:21]2[CH:20]=[CH:19][C:18]([O:17][C:9](=[O:16])[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:25][CH:24]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 2205594-formylphenyl benzoate

Product 1

HCID 67977427HCID 67977427, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 500 ml flask were added 45.6 grams (0.374 mol) 4-hydroxylbenzaldehyde, 150 ml of acetone and 25.8 grams (0.187 mol) potassium carbonate. Then, 52.1 ml (0.449 mol) of benzoyl chloride (BzCl) was added therein dropwise slowly at a temperature of about 0° C. After the addition, the mixture was warmed up to room temperature and the reaction lasted 2 hours. The residue was extracted 3 times with ethyl acetate (150 ml×3). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated till dry to obtain 76.08 grams (0.336 mol) 4-benzoyloxybenzaldehyde. Next, 35.7 ml (0.37 mol) of 4-fluoroaniline was added dropwise to a solution of the obtained 4-benzoyloxybenzaldehyde in 300 ml of ethyl acetate. The reaction lasted 1 hours. The reaction mixture was filtered. The obtained solid was recrystallized from anhydrous ethanol to obtain 60.3 grams (0.189 mol) white solid, namely compound II-1. 1H NMR (400 MHz, CDCl3): δ 7.09-7.14 (m, 2H, Cpr-H), 7.23-7.28 (m, 2H, Cpr-H), 7.37-7.39 (m, 2H, Cpr-H), 7.54-7.59 (m, 2H, Cpr-H), 7.67-7.71 (m, 1H, Cpr-H), 7.99-8.02 (m, 2H, Cpr-H), 8.24-8.26 (m, 2H, Cpr-H), 8.49 (s, 1H, —CH—).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customThe obtained solid was recrystallized from anhydrous ethanol

Sources & evidence

ORD record
ord-fe993c84620c4d4e9e6fcb1b8ddaf572
Source dataset
uspto-grants-2014_01
Patent number
US08623855B2

Reaction notes

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