Hydrochloric Acid → 2'-Hydroxy-2-[bis-(3-fluorophenyl)phosphino]biphenyl

HRID 481815

Reaktionsgleichung

Reaktionsgleichung von HRID 481815
Cl[P:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5]2[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=2[O:3]1.[F:16][C:17]1[CH:18]=[C:19]([Mg]Br)[CH:20]=[CH:21][CH:22]=1.O.Cl>O1CCCC1.C(OCC)(=O)C>[OH:3][C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[P:2]([C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([F:16])[CH:22]=1)[C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([F:16])[CH:22]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 898166H-Dibenz[c,e][1,2]oxaphosphorin, 6-chloro-HCID 178505773HCID 178505773, Verbindung

Produkt 1

HCID 190673292'-Hydroxy-2-[bis-(3-fluorophenyl)phosphino]biphenylAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

16.4 g (70 mmol) of 6-chloro-6H-dibenz[c,e][1,2]oxaphosphorine in 80 ml of anhydrous tetrahydrofuran are introduced, in an argon atmosphere with stirring, and a 2M solution of 140 mmol of 3-fluorophenylmagnesium bromide in tetrahydrofuran is added dropwise. The temperature increases in the course of this from 25° to 45° C. The mixture is then stirred for 12 hours at 65° C., cooled to room temperature and 100 ml of water and 100 ml of ethyl acetate are added. The mixture is neutralized with dilute hydrochloric acid, the organic phase is separated off, dried with sodium sulfate and concentrated under reduced pressure. 25.8 g of colorless oil are obtained. By crystallization with methanol/water, 10:1, 19.8 g (71%) of colorless crystals having melting point 161° to 163° C. are obtained.

Aufarbeitung

  1. temperatureThe temperature increases in the course of this from 25° to 45° C
  2. stirringThe mixture is then stirred for 12 hours at 65° C.
  3. customthe organic phase is separated off
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1a9e888934264b38a28efb4b76071477
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05789623

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