Cesium fluoride → Methyl 6-benzyloxy-5-tert-butyl-4'-methyl-3-biphenylcarboxylate

HRID 2377198Notes

Reaction equation

HRID 2377198 reaction equation
[CH2:1]([O:8][C:9]1[C:18](I)=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[C:20]([CH3:23])([CH3:22])[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.[F-].[Cs+]>O1CCOCC1.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>[CH2:1]([O:8][C:9]1[C:18]([C:28]2[CH:29]=[CH:30][C:25]([CH3:24])=[CH:26][CH:27]=2)=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[C:20]([CH3:23])([CH3:22])[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 79799Tolylboronic acidHCID 12084816Methyl 4-benzyloxy-3-tert-butyl-5-iodobenzoate

Product 1

HCID 12084817Methyl 6-benzyloxy-5-tert-butyl-4'-methyl-3-biphenylcarboxylateYield 83%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

12 g (28 mmol) of methyl 4-benzyloxy-3-tert-butyl-5-iodobenzoate are dissolved with 5.8 g (42 mmol) of 4-methylbenzeneboronic acid and 12.7 g (84 mmol) of caesium fluoride in 400 mL of dioxane. The reaction medium is degassed with a flow of nitrogen for 15 minutes, and 1.7 g (1.4 mmol) of tetrakis(triphenylphosphine)palladium are then added. The reaction medium is refluxed for 4 hours and then cooled and hydrolysed. After extraction with ethyl acetate, the organic phase is filtered and concentrated. The residue is purified by chromatography (eluent: 98 heptane/2 ethyl acetate): a colorless oil is obtained (m=9 g, yield=83%).

Workup

  1. customThe reaction medium is degassed with a flow of nitrogen for 15 minutes
  2. temperatureThe reaction medium is refluxed for 4 hours
  3. temperaturecooled
  4. extractionAfter extraction with ethyl acetate
  5. filtrationthe organic phase is filtered
  6. concentrationconcentrated
  7. customThe residue is purified by chromatography (eluent: 98 heptane/2 ethyl acetate)
  8. customa colorless oil is obtained (m=9 g, yield=83%)

Sources & evidence

ORD record
ord-085ac38486c845cb925cf3f08237060b
Source dataset
uspto-grants-2008_12
Patent number
US07468457B2

Reaction notes

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