6H-Dibenz[c,e][1,2]oxaphosphorin, 6-chloro- → HCID 19067337, compound

HRID 481818Notes

Reaction equation

HRID 481818 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.[C:16]1([CH3:24])[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Mg]Br.[C:25]1([Mg]Br)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CC1C=CC=CC=1C.O1CCCC1.C(OCC)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[PH:2][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:24]1[CH:29]=[CH:30][CH:25]=[CH:26][C:27]=1[CH3:28]

Participants

7

Reactant 3

HCID 898166H-Dibenz[c,e][1,2]oxaphosphorin, 6-chloro-HCID 178418255HCID 178418255, compoundHCID 178424303HCID 178424303, compound

Product 1

HCID 19067337HCID 19067337, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 7237O-XyleneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

16.4 g (70 mmol) of 6-chloro-6H-dibenz[c,e][1,2]oxaphosphorine in 50 ml of anhydrous o-xylene are introduced, in an argon atmosphere with stirring, and a solution of 70 mmol of 2-tolylmagnesium bromide in tetrahydrofuran are added dropwise at -10° C. The mixture is slowly heated to 25° C. and stirred for 3 hours. A solution of 70 mmol of phenylmagnesium bromide in 50 ml of diethyl ether is added dropwise and the mixture is then heated to 65° C., the diethyl ether being distilled off. The mixture is stirred for a further 2 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. 25.8 g of colorless crystals are obtained. By recrystallization from methanol/water, 10:1, 20.4 g (79%) of colorless crystals having melting point 98 at 101° C. are obtained.

Workup

  1. stirringstirred for 3 hours
  2. temperaturethe mixture is then heated to 65° C.
  3. distillationthe diethyl ether being distilled off
  4. stirringThe mixture is stirred for a further 2 hours at 120° C.
  5. temperaturecooled to room temperature
  6. addition100 ml of water are added
  7. customthe organic phase is separated off
  8. dry with materialdried with sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-47eb2121ee24493fbd008691c1b29086
Source dataset
uspto-grants-1998_08
Patent number
US05789623

Reaction notes

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