6H-Dibenz[c,e][1,2]oxaphosphorin, 6-chloro- → HCID 19067334, compound

HRID 481821Notes

Reaction equation

HRID 481821 reaction equation
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]([F:31])([F:30])[C:18]1[CH:19]=[C:20]([Mg]Br)[CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1>CC1C=CC=CC=1C.O1CCCC1>[F:16][C:17]([F:31])([F:30])[C:18]1[CH:19]=[C:20]([P:2]([C:20]2[CH:21]=[C:22]([C:24]([F:27])([F:25])[F:26])[CH:23]=[C:18]([C:17]([F:16])([F:31])[F:30])[CH:19]=2)[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[OH:3])[CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1

Participants

5

Reactant 2

HCID 898166H-Dibenz[c,e][1,2]oxaphosphorin, 6-chloro-HCID 178506227HCID 178506227, compound

Product 1

HCID 19067334HCID 19067334, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

23.5 g (0.1 mol) of 6-chloro-6H-dibenz[c,e][1,2]oxaphosphorine in 200 ml of anhydrous o-xylene at 80° C. are introduced, in an argon atmosphere with stirring, and a solution of 0.23 mol of 3,5-di(trifluoromethyl)phenylmagnesium bromide in 300 ml of tetrahydrofuran is added dropwise. Tetrahydrofuran is distilled off and the temperature is slowly increased to 120° C. in the course of this. The mixture is then stirred for 3 hours at 120° C., cooled to room temperature, and 100 ml of water 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. 61.0 g of black solid are obtained. By recrystallization from heptane, with addition of activated carbon, and subsequent hot filtration, 37.2 g (59%) of pale yellow crystals having melting point 120° to 121° C. are obtained.

Workup

  1. distillationTetrahydrofuran is distilled off
  2. stirringThe mixture is then stirred for 3 hours at 120° C.
  3. temperaturecooled to room temperature
  4. addition100 ml of water are added
  5. customthe organic phase is separated off
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6fa06fa064dd409c8550f6759ba1bb36
Source dataset
uspto-grants-1998_08
Patent number
US05789623

Reaction notes

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