Hydrochloric Acid → HCID 53899106, compound

HRID 1816767Notes

Reaction equation

HRID 1816767 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:15][C@H:16]1[O:21][C@@H:20]([CH3:22])[CH2:19][NH:18][CH2:17]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl>C1(C)C=CC=CC=1.CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C.ClCCl>[CH3:22][C@H:20]1[O:21][C@@H:16]([CH3:15])[CH2:17][N:18]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)[CH2:19]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 950934-Bromo-4'-hydroxybiphenylHCID 6415002,6-Dimethylmorpholine, cis-HCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 53899106HCID 53899106, compound

Reagents, catalysts & solvents 3

HCID 178424406HCID 178424406, compoundCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromo-4′-hydroxy-1,1′-biphenyl (5 g), cis-2,6-dimethylmorpholine, dichlorobis(tri-o-tolylphosphine)-palladium(II) and lithium bis(trimethylsilyl)amide (1.0 M solution in hexanes) (44 ml) in toluene (25 ml) was stirred for 6 hours at 100° C. The reaction mixture was added to a mixture of 1.0 mol/l hydrochloric acid and dichloromethane. The organic layer was washed with 1.0 mol/l hydrochloric acid, sodium hydrogen carbonate solution and sodium chloride solution. The organic layer was taken and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (50:1 dichloromethane-methanol elution) to give 4′-(cis-2,6-dimethylmorpholin-4-yl)-1,1′-biphenyl-4-ol (1.49 g).

Workup

  1. washThe organic layer was washed with 1.0 mol/l hydrochloric acid, sodium hydrogen carbonate solution and sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe magnesium sulfate was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (50:1 dichloromethane-methanol elution)

Sources & evidence

ORD record
ord-c40985532c254a62a97aae765a7e7bf5
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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