Ethanol → HCID 17858301, compound

HRID 2251140Notes

Reaction equation

HRID 2251140 reaction equation
FC(F)(F)S(O[C:7]1[CH:15]=[C:14]2[C:10]([C:11]([CH3:35])([CH3:34])[CH2:12][C:13]32[C:23]2[C:18](=[CH:19][CH:20]=[C:21](OS(C(F)(F)F)(=O)=O)[CH:22]=2)[C:17]([CH3:33])([CH3:32])[CH2:16]3)=[CH:9][CH:8]=1)(=O)=O.[C:38]([C:41]1[CH:46]=[CH:45][C:44](B(O)O)=[CH:43][CH:42]=1)(=[O:40])[CH3:39].C(=O)([O-])[O-].[Na+].[Na+].[C:56]1(C)[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1.[CH2:63]([OH:65])[CH3:64]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:63]([C:56]1[CH:61]=[CH:60][C:59]([C:21]2[CH:22]=[C:23]3[C:18]([C:17]([CH3:33])([CH3:32])[CH2:16][C:13]43[C:14]3[C:10](=[CH:9][CH:8]=[C:7]([C:44]5[CH:45]=[CH:46][C:41]([C:38](=[O:40])[CH3:39])=[CH:42][CH:43]=5)[CH:15]=3)[C:11]([CH3:34])([CH3:35])[CH2:12]4)=[CH:19][CH:20]=2)=[CH:58][CH:57]=1)(=[O:65])[CH3:64]

Participants

7

Reactant 5

HCID 702EthanolHCID 1140TolueneHCID 10340Sodium CarbonateHCID 37021224-Acetylphenylboronic acidHCID 17858312HCID 17858312, compound

Product 1

HCID 17858301HCID 17858301, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

2.5 g of 6,6′-bis(trifluoromethanesulphonyloxy)-3,3,3′,3′-tetramethyl-1,1′-spirobiindane, 2.2 g of 4-acetylphenylboronic acid, 12 ml of 2M sodium carbonate and 0.40 g of tetrakis(triphenylphosphine)palladium(0) were added to a solvent mixture of 50 ml of toluene and 30 ml of ethanol, and then refluxing carried out for 12 hours under nitrogen so that a Suzuki coupling reaction was conducted and, by treatment in the normal way, 1.5 g of 6,6′-bis(4-acetylphenyl)-3,3,3′,3′-tetramethyl-1,1′-spirobiindane was obtained. 1.50 g of this diacetyl derivative was reacted with 1.26 g of 8-amino-7-quinolinecarbaldehyde and 0.9 g of potassium hydroxide in dioxane at 60° C. and, by treatment in the normal way, Phen-4 (1.40 g) shown below was obtained. 1H-NMR (CDCl3, ppm): 9.21 (d, 2H), 8.35 (d, 4H), 8.25 (t, 4H), 8.09 (d, 2H), 7.80−7.59 (m, 12H), 7.34 (d, 2H), 7.24 (d, 2H), 2.46 (d, 4H), 1.52 (s, 6H), 1.46 (s, 6H)

Workup

  1. temperaturerefluxing
  2. customcarried out for 12 hours under nitrogen so that a Suzuki coupling reaction

Sources & evidence

ORD record
ord-2c9931715ec54f318f1001a25d5739b9
Source dataset
uspto-grants-2008_01
Patent number
US07318966B2

Reaction notes

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