Sodium Carbonate → 9-Fluoro-7-(2,3-difluoro4-octyloxyphenyl)-2-octyloxyphenanthrene

HRID 564680Notes

Reaction equation

HRID 564680 reaction equation
Br[C:2]1[CH:15]=[C:14]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:10][C:11]=3[CH:12]=[C:13]2[F:16])=[CH:4][CH:3]=1.[F:26][C:27]1[C:32]([F:33])=[C:31]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:30]=[CH:29][C:28]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:16][C:13]1[C:14]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:10][C:11]=3[CH:12]=1)=[CH:4][CH:3]=[C:2]([C:28]1[CH:29]=[CH:30][C:31]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[C:32]([F:33])[C:27]=1[F:26])[CH:15]=2

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10850744(2,3-Difluoro-4-(octyloxy)phenyl)boronic acidHCID 221125847-Bromo-9-fluoro-2-octyloxyphenanthrene

Product 1

HCID 542800789-Fluoro-7-(2,3-difluoro4-octyloxyphenyl)-2-octyloxyphenanthrene

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

From 7-bromo-9-fluoro-2-octyloxyphenanthrene by reaction with 2,3-difluoro4-octyloxyphenylboronic acid, sodium carbonate and tetrakis(triphenylphosphine)-palladium (0) in toluene/ethanol/H2O.

Sources & evidence

ORD record
ord-5da2f766f79d4a14b7538a3f80a8f37d
Source dataset
uspto-grants-2001_01
Patent number
US06168838A

Reaction notes

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