Hydrochloric Acid → 1,1'-Binaphthalene, 2,2'-dimethyl-

HRID 1721537Notes

Reaction equation

HRID 1721537 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[Mg]Br.Br[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[CH3:25].P.C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(COC2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2OCP(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[CH3:25]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 24404Phosphine2×HCID 757541-Bromo-2-methylnaphthaleneHCID 821241,4-Bis(diphenylphosphino)butaneHCID 118285682,2'-Bis(diphenylphosphinomethoxy)-1,1'-binaphthylHCID 178422613HCID 178422613, compound

Product 1

HCID 1417481,1'-Binaphthalene, 2,2'-dimethyl-

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

2-Methyl-1-naphthylmagnesium bromide prepared according to Example 1 in toluene is added in the absence of air and moisture to a suspension, heated to 70° to 80° C., of 31.0 g (0.14 mol) of 1-bromo-2-methylnaphthalene, 0.0014 mol of the phosphine of the formula (I) 1,4-bis(diphenylphosphino)butane; 2,2'-bis(diphenylphosphinomethoxy)-1,1'-binaphthyl! or 0.0028 mol of the phosphine of the formula (II) (triphenylphosphine) and 0.31 g (0.0014 mol) of palladium(II) acetate in 50 ml of toluene. The mixture is then heated at 80° C. for another hour, cooled to 25° C., and 100 ml of water and 50 ml of 2N hydrochloric acid are added in succession to the reaction mixture. The phases are separated, the aqueous phase is extracted with 50 ml of toluene, and the combined organic phases are concentrated in vacuo. Distillation of the oily, brown residue in a high vacuum gives a pale yellow oil having a boiling point of 175° to 180° C./0.1 to 0.2 mbar. The yields can be found in Table 1 below.

Workup

  1. additionis added in the absence of air and moisture to a suspension
  2. temperaturecooled to 25° C.
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with 50 ml of toluene
  5. concentrationthe combined organic phases are concentrated in vacuo
  6. distillationDistillation of the oily, brown residue in a high vacuum
  7. customgives a pale yellow oil
  8. customThe yields can

Sources & evidence

ORD record
ord-4366f3247c8f4e719e3b89237ebb09a7
Source dataset
uspto-grants-1996_04
Patent number
US05510554

Reaction notes

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