Hydrochloric Acid → HCID 19067314, compound

HRID 481820Notes

Reaction equation

HRID 481820 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1Br.Cl[P:21]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[C:24]2[CH:31]=[CH:32][CH:33]=[CH:34][C:23]=2O1.Cl.C([O:38]CC)C>CCCCCC.CC1C=CC=CC=1C.O>[CH:31]1[C:24]2[C:25]3[C:30]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[OH:38])=[CH:29][CH:28]=[CH:27][C:26]=3[PH:21][C:23]=2[CH:34]=[CH:33][CH:32]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 830602,2'-DibromobiphenylHCID 898166H-Dibenz[c,e][1,2]oxaphosphorin, 6-chloro-HCID 178418339Butyllithium

Product 1

HCID 19067314HCID 19067314, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 7237O-XyleneSolventHCID 8058HexaneSolvent

Conditions

Temperature
20 °C

Procedure

46 ml of a 1.6M solution of butyllithium in hexane are added dropwise to a solution of 11.4 g (36.54 mmol) of 2,2'-dibromobiphenyl in 60 ml of diethyl ether. The mixture is then stirred for 24 hours at 20° C. To this is then added, at 0C, a solution of 8.6 g (36.5 mmol) of 6-chloro-6H-dibenz[c,e][1,2]oxaphosphorine in 30 ml of o-xylene. The mixture is then stirred for a further 2 hours at 25° C. and 3 hours at 50° C. The mixture is cooled to room temperature and 100 ml of water are carefully added. The mixture is neutralized with dilute hydrochloric acid, the organic phase is separated off, dried with sodium sulfate and concentrated under reduced pressure. By crystallization of the residue with 2-butanone, 11.8 g (90%) of colorless crystals having melting point 152° to 155° C. are obtained.

Workup

  1. stirringThe mixture is then stirred for a further 2 hours at 25° C. and 3 hours at 50° C
  2. temperatureThe mixture is cooled to room temperature
  3. customthe organic phase is separated off
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customBy crystallization of the residue with 2-butanone, 11.8 g (90%) of colorless crystals
  7. customare obtained

Sources & evidence

ORD record
ord-201aee0ec3574296beec9eea62e647de
Source dataset
uspto-grants-1998_08
Patent number
US05789623

Reaction notes

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