Sodium Carbonate → HCID 10620805, compound

HRID 343253Notes

Reaction equation

HRID 343253 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:5]=[CH:4][C:3]=1B(O)O.[Br:21][C:22]1[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.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>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([C:3]2[CH:4]=[CH:5][C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[C:7]([F:8])[C:2]=2[F:1])=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzene2×HCID 10850744(2,3-Difluoro-4-(octyloxy)phenyl)boronic acid

Product 1

HCID 10620805HCID 10620805, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of 2,3-difluro-4-octoxyphenylboronic acid (5) (8.29 g, 0.029 mol) in dimethoxyethane (40 ml) was added to a solution of 4-bromoiodobenzene (6.80 g, 0.024 mol) and tetrakis(triphenylphosphine)palladium (0) (1.4 8 g. 1.29 mmol) in dimethoxyethane (40 ml) under nitrogen. To this, 2M sodium carbonate (60 ml) was added. The stirred mixture was refluxed gently. Progress of the reaction was carefully monitored using tic until the 4-bromoiodobenzene had reacted completely (usually 4-5hr). The layers were separated and the aqueous layer once more extracted with ether. The combined organic layers were washed with brine and dried (MgSO4). The solvent was removed in vacuo and the residue purified by column chromatography (silica gel/petroleum fraction (bp 40°-60° C.) - ethyl acetate, 9:1) to give a white solid which was recrystallised from pentane (-20° C.) to yield colourless crystals.

Workup

  1. temperatureThe stirred mixture was refluxed gently
  2. customhad reacted completely (usually 4-5hr)
  3. customThe layers were separated
  4. extractionthe aqueous layer once more extracted with ether
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed in vacuo
  8. customthe residue purified by column chromatography (silica gel/petroleum fraction (bp 40°-60° C.) - ethyl acetate, 9:1)
  9. customto give a white solid which
  10. customwas recrystallised from pentane (-20° C.)
  11. customto yield colourless crystals

Sources & evidence

ORD record
ord-66e3316ba47240538a7c235187b81555
Source dataset
uspto-grants-1999_01
Patent number
US05861109

Reaction notes

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