HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Dichloromethane → 2-Fluoro-3,6-di(4-octyloxyphenyl)pyridine

HRID 1780558
Notes
Print preview

Reaction equation

HRID 1780558 reaction equation
[F:1][C:2]1[C:7](B(O)O)=[CH:6][CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:13][CH:12]=2)[N:3]=1.Br[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+].ClCCl>C(O)C.C1C=CC=CC=1.O.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>[F:1][C:2]1[C:7]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:29][CH:28]=2)=[CH:6][CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:13][CH:12]=2)[N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 145298p-Bromophenyl octyl etherHCID 190469502-Fluoro-6-(4-octyloxyphenyl)pyridine-3-boronic acid

Product 1

HCID 190469512-Fluoro-3,6-di(4-octyloxyphenyl)pyridineYield 49.4%

Reagents, catalysts & solvents 4

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 241BenzeneSolvent
HCID 702EthanolSolvent
HCID 962WaterSolvent2×

Procedure

3.35 g (10.00 mmol) of 2-fluoro-6-(4-octyloxyphenyl)pyridine-3-boronic acid in 45 ml of ethanol are refluxed together with 2.85 g (10.00 mmol) of 1-bromo-4-octyloxybenzene and 0.37 g (0.31 mmol) of tetrakis(triphenylphosphine)palladium in 60 ml of benzene and 3.18 g (30.00 mmol) of sodium carbonate in 12 ml of water for 20 hours. After distributing the reaction mixture between water and dichloromethane, the organic phase is washed with sodium chloride solution, dried over sodium sulfate, filtered and concentrated. Purification of the residue by chromatography (silica gel, dichloromethane) and recrystallization from acetonitrile give 2.5 g of 2-fluoro-3,6-di(4-octyloxyphenyl)pyridine. ##STR30##

Workup

  1. washthe organic phase is washed with sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the residue
  6. customby chromatography (silica gel, dichloromethane) and recrystallization from acetonitrile

Sources & evidence

ORD record
ord-16cb24c04b964b758ce53dcb997dd6d7
Source dataset
uspto-grants-1997_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05630962

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes