Hydrochloric Acid → HCID 19067324, compound

HRID 481817Notes

Reaction equation

HRID 481817 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.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Mg]Br.[C:26]1([Mg]Br)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl>O1CCCC1.O>[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:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[O:17][CH3:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 898166H-Dibenz[c,e][1,2]oxaphosphorin, 6-chloro-HCID 178418255HCID 178418255, compoundHCID 178489560HCID 178489560, compound

Product 1

HCID 19067324HCID 19067324, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
25 °C

Procedure

23.5 g (100 mmol) of 6-chloro-6H-dibenz[c,e][1,2]oxa-phosphorine in 50 ml of anhydrous tetrahydrofuran are introduced, in an argon atmosphere with stirring, and a solution of 100 mmol of 2-methoxyphenylmagnesium bromide in tetrahydrofuran is added dropwise at -10° C. The mixture is slowly heated to 25° C. and stirred for 3 hours. A solution of 100 mmol of phenylmagnesium bromide in 150 ml of tetrahydrofuran is added dropwise and the mixture is then stirred for 5 hours at 65° C. The mixture is 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. 38.0 g of colorless oil are obtained. By crystallization with methanol/water, 10:1, 32.7 g (86%) of colorless crystals having melting point 137° to 139° C. are obtained.

Workup

  1. stirringstirred for 3 hours
  2. stirringthe mixture is then stirred for 5 hours at 65° C
  3. temperatureThe mixture is cooled to room temperature
  4. customthe organic phase is separated off
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d6bae647cf144f7ea83ed44f7c61ee34
Source dataset
uspto-grants-1998_08
Patent number
US05789623

Reaction notes

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