Sodium Carbonate → HCID 58629947, compound

HRID 1391743Notes

Reaction equation

HRID 1391743 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]([O:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:16]([CH3:27])[CH:15]=2)[CH2:9][CH2:10][CH2:11][CH3:12])[CH:5]=[CH:6][CH:7]=1.[F:28][C:29]([F:40])([F:39])[C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.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>[CH3:27][C:16]1[CH:15]=[C:14]([O:13][CH:8]([C:4]2[CH:3]=[C:2]([C:33]3[CH:34]=[CH:35][C:30]([C:29]([F:40])([F:39])[F:28])=[CH:31][CH:32]=3)[CH:7]=[CH:6][CH:5]=2)[CH2:9][CH2:10][CH2:11][CH3:12])[CH:19]=[CH:18][C:17]=1[O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 58629854HCID 58629854, compound

Product 1

HCID 58629947HCID 58629947, compoundYield 61.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl [(4-{[1-(3-bromophenyl)pentyl]oxy}-2-methylphenyl)oxy]acetate (200 mg, 0.46 mmol) was dissolved in dry THF (3 mL), and treated with 4-(trifluoromethyl)benzeneboronic acid (104 mg, 0.55 mmol), Pd(PPh3)4 (53 mg, 0.046 mmol) and sodium carbonate (146 mg, 1.38 mmol) in water (2 mL). The mixture was then heated at 70° C. for 3 hours, cooled to rt and partitioned between EtOAc and water. The layers were separated and the organic layer washed with brine, dried (Na2SO4) and concentrated to give a brown oil. Purification by Biotage™ chromatography (silica, 40 g cartridge) eluting with petroleum ether 40-60° C.:EtOAc (19:1) afforded the title compound as a colourless gum (142 mg).

Workup

  1. temperaturecooled to rt
  2. custompartitioned between EtOAc and water
  3. customThe layers were separated
  4. washthe organic layer washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give a brown oil
  8. customPurification by Biotage™ chromatography (silica, 40 g cartridge)
  9. washeluting with petroleum ether 40-60° C.

Sources & evidence

ORD record
ord-81f6761888724e63b0e491da787917f5
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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