4'-Fluoroacetophenone → HCID 3664387, compound

HRID 342379Notes

Reaction equation

HRID 342379 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=O)[CH3:25])=[CH:20][CH:19]=1>>[Cl:16][C:13]1[CH:12]=[C:3]2[C:2](=[CH:15][CH:14]=1)[N:1]=[C:24]([C:21]1[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=1)[CH:25]=[C:4]2[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 98284'-FluoroacetophenoneHCID 128702-Amino-5-chlorobenzophenone

Product 1

HCID 3664387HCID 3664387, compound

Conditions

Temperature
165 °C

Procedure

A three-necked, 2 L round-bottomed flask equipped with a thermometer, a mechanical stirrer and a distillation unit fitted with a nitrogen inlet valve was charged with 2-amino-5-chlorobenzophenone (695.0 g, 3.00 mol), and 4'-fluoroacetophenone (456.0 g, 3.30 mol), p-tosic acid (47.62 g, 0.25 mol). The reaction mixture was heated under nitrogen at 165° C. (44 h). The yellow 4'-acetophenone that co-distilled with the water was separated and reintroduced to the reaction mixture throughout the heating period. The mixture was further heated, to 190° C. (2 h). The mixture was cooled to 120° C. and was poured into 95% ethanol (10 L) while vigorously stirring with a mechanical stirring rod set up. The mixture was filtered and the precipitate was washed with ethanol (1 L). The solid was dried in a vacuum oven at 80° C. (16 h). Yield 969 g, 97%; mp 141.0°-142.1° C.

Workup

  1. customA three-necked, 2 L round-bottomed flask equipped with a thermometer, a mechanical stirrer
  2. customa distillation unit fitted with a nitrogen inlet valve
  3. customThe yellow 4'-acetophenone that co-distilled with the water was separated
  4. additionreintroduced to the reaction mixture throughout the heating period
  5. customto 190° C.
  6. custom(2 h)
  7. temperatureThe mixture was cooled to 120° C.
  8. additionwas poured into 95% ethanol (10 L)
  9. filtrationThe mixture was filtered
  10. washthe precipitate was washed with ethanol (1 L)
  11. customThe solid was dried in a vacuum oven at 80° C. (16 h)

Sources & evidence

ORD record
ord-3f901b92174a4152aeab090af24913fc
Source dataset
uspto-grants-1999_01
Patent number
US05858907

Reaction notes

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