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

HRID 369558노트

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HRID 369558 반응식
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

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 10821PhenylacetyleneHCID 11776TriphenylphosphineHCID 74951(4-Bromophenyl)(4-fluorophenyl)methanone2회

생성물 1

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

시약·촉매·용매 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 8471Triethylamine용매

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온도
23 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c4709ef325e24f80b7a8bb3c436bd115
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06139920

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