Hydrochloric Acid → 4-Fluoro-4'-(phenylethynyl)benzophenone

HRID 369558

反応式

HRID 369558 の反応式
Br[C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[C:17]1([C:23]#[CH:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(N(CC)CC)C>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([C:5]2[CH:15]=[CH:16][C:2]([C:24]#[C:23][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:3][CH:4]=2)=[O:7])=[CH:9][CH:10]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 10821PhenylacetyleneHCID 11776TriphenylphosphineHCID 74951(4-Bromophenyl)(4-fluorophenyl)methanone2 回

生成物 1

HCID 40956574-Fluoro-4'-(phenylethynyl)benzophenone

試薬・触媒・溶媒 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 8471Triethylamine溶媒

反応条件

温度
23 °C

実験手順

4-Fluoro-4'-phenylethynylbenzophenone was synthesized by the cuprous iodide catalyzed coupling of 4-bromo-4'-fluorobenzophenone. More specifically, 4-bromo-4'-fluorobenzophenone (30 grams, 0.11 mol), phenylacetylene (11 grams, 0.11 mol), triphenylphosphine (0.2 gram), cuprous iodide (0.1 gram), bis(triphenylphosphine) palladium dichloride (0.1 gram) and 450 milliliters of triethylamine were charged to a 500 milliliter flask equipped with a mechanical stirrer, N2 inlet, and reflux condenser. The mixture was heated to reflux for 4 hours, cooled to 23° C., and stirred for an additional 16 hours. The mixture was then poured into water acidified with HCl and the precipitate was collected by filtration. Recrystallization from acetone gave 23 grams (75 percent yield) of the desired product.

後処理

  1. customequipped with a mechanical stirrer, N2 inlet
  2. temperaturereflux condenser
  3. temperatureThe mixture was heated
  4. temperatureto reflux for 4 hours
  5. filtrationthe precipitate was collected by filtration
  6. customRecrystallization from acetone

出典と根拠

ORDレコード
ord-c4709ef325e24f80b7a8bb3c436bd115
出典データセット
uspto-grants-2000_10
特許番号
US06139920

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