Hydrochloric Acid → HCID 58940057, compound

HRID 988030Notes

Reaction equation

HRID 988030 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:7][C:6]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:5][C:4]=1B(O)O.Br[C:21]1[CH:22]=[C:23]([CH:29]=[CH:30][CH:31]=1)[CH:24]=[CH:25][C:26]([OH:28])=[O:27].C(=O)([O-])[O-].[K+].[K+].Cl>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.C(OCC)(=O)C.O.COCCOC>[C:9]([C:8]1[C:3]([O:2][CH3:1])=[C:4]([C:30]2[CH:31]=[CH:21][CH:22]=[C:23]([CH:24]=[CH:25][C:26]([OH:28])=[O:27])[CH:29]=2)[CH:5]=[C:6]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 362513-(3-Bromophenyl)acrylic acidHCID 15405941HCID 15405941, compound

Product 1

HCID 58940057HCID 58940057, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.2 g (8.3 mmol) of 2-methoxy-3,5-di-tert-butylphenylboronic acid, 942 mg (4.15 mmol) of 3-bromocinnamic acid and 70 ml of DME were introduced into a three-necked flask under a stream of nitrogen. 11.4 ml of aqueous potassium carbonate solution (2M) were added dropwise and the reaction medium was degassed. 144 mg (0.12 mmol) of tetrakistriphenylphosphinepalladium(0) were then added and the mixture was refluxed for 20 hours. Water and ethyl acetate were added to the reaction medium and this mixture was acidified to pH 1 with hydrochloric acid. The organic phase was separated out after settling had taken place, washed with water, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (75/25). After evaporation of the solvents, 990 mg (66%) of 3-(3′,5′-di-tert-butyl-2′-methoxy-3-biphenylyl)acrylic acid having a melting point of 182°-3° C. were collected.

Workup

  1. customthe reaction medium was degassed
  2. temperaturethe mixture was refluxed for 20 hours
  3. customThe organic phase was separated out
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue obtained
  8. customwas purified by chromatography on a column of silica
  9. washeluted with a mixture of heptane and ethyl acetate (75/25)
  10. customAfter evaporation of the solvents, 990 mg (66%) of 3-(3′,5′-di-tert-butyl-2′-methoxy-3-biphenylyl)acrylic acid having a melting point of 182°-3° C.
  11. customwere collected

Sources & evidence

ORD record
ord-64458f1e2afc4cff92dfc17505320bb7
Source dataset
uspto-grants-2003_10
Patent number
US06632963B1

Reaction notes

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