Potassium Phosphate, Tribasic → HCID 58897803, compound

HRID 2357864Notes

Reaction equation

HRID 2357864 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[CH2:9][CH:8]=[C:7]2[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:17]1([C:23]2[C:31]3[C:26](=[C:27]([OH:32])[CH:28]=[CH:29][CH:30]=3)[CH2:25][CH:24]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1N(C)C)(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].O.C1(C)C=CC=CC=1>[C:11]1([C:7]2[C:6]3[C:10](=[C:2]([O:32][C:27]4[CH:28]=[CH:29][CH:30]=[C:31]5[C:26]=4[CH2:25][CH:24]=[C:23]5[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:3]=[CH:4][CH:5]=3)[CH2:9][CH:8]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27349362-Di-tert-butylphosphino-2'-(N,N-dimethylamino)biphenylHCID 58897785HCID 58897785, compoundHCID 58897793HCID 58897793, compound

Product 1

HCID 58897803HCID 58897803, compound

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Under an argon atmosphere, to a mixture of 6.90 g (25.5 mmol) of 7-bromo-3-phenyl-1H-indene, 5.30 g (25.5 mmol) of 3-phenyl-1H-inden-7-ol, 10.8 g (51 mmol) K3PO4, and 100 ml of toluene, a mixture of 300 mg (0.52 mmol) Pd(dba)2 and 348 mg (1.02 mmol) of N-{2′-[di(tert-butyl)phosphino][1,1′-biphenyl]-2-yl}-N,N-dimethylamine was added. This mixture was stirred for 8 hours at 100° C. Then, 300 ml of water was added, the organic layer was separated, and the aqueous layer was extracted with 3×75 ml of CH2Cl2. The combined extract was washed with 2×100 ml of water, dried over K2CO3, and evaporated to dryness. The analytically pure product, bis(3-phenyl-1H-inden-7-yl)ether, was obtained using flash chromatography on Silica Gel 60 (40-63 μm, d 50 mm, 1250 mm, eluant: CH2Cl2). Yield, 3.56 g (35%) of a white solid.

Workup

  1. additionwas added
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with 3×75 ml of CH2Cl2
  4. extractionThe combined extract
  5. washwas washed with 2×100 ml of water
  6. dry with materialdried over K2CO3
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-29d06ba7199f4d2f933c6768cdd726a0
Source dataset
uspto-grants-2010_07
Patent number
US07763562B2

Reaction notes

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