Hydrochloric Acid → Methyl (4'-hydroxybiphenyl-3-yl)acetate

HRID 2076592Notes

Reaction equation

HRID 2076592 reaction equation
C(=O)([O-])[O-].[K+].[K+].CC1(C)C(C)(C)OB([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)O1.Br[C:24]1[CH:25]=[C:26]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:27]=[CH:28][CH:29]=1.Cl>CN(C)C(=O)C.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>[OH:21][C:18]1[CH:17]=[CH:16][C:15]([C:28]2[CH:29]=[CH:24][CH:25]=[C:26]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:27]=2)=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 11746402Methyl 2-(3-bromophenyl)acetate

Product 1

HCID 59219036Methyl (4'-hydroxybiphenyl-3-yl)acetateYield 67%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21534740N,N-Dimethylacetamide--water (1/1)Solvent

Conditions

Temperature
110 °C

Procedure

Tetrakis(triphenylphosphine)palladium (0) (1.00 g, 0.88 mmol) and potassium carbonate (4.80 g, 37.0 mmol) were added to a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (3.84 g, 17.5 mmol) and methyl (3-bromophenyl)acetate (4.00 g, 17.5 mmol) which was synthesized according to the method described in literature (Muller, R. N. et al., Eur. J. Org. Chem., 2002, vol. 23, pp. 3966-3973) in a mixture of N,N-dimethylacetamide-water (10:1, 66 ml), and the mixture was stirred at 110° C. for 6 hours. After the reaction mixture was poured into 0.2N hydrochloric acid and the mixture was extracted with ethyl acetate, the organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=2/1) to give methyl (4′-hydroxy-1,1′-biphenyl-3-yl)acetate (2.83 g, yield: 67%).

Workup

  1. customwas synthesized
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic layer was successively washed with water
  4. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  5. customThe residue obtained
  6. customby removing the solvent under reduced pressure
  7. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-1ea0b1dd82e641009b468057c51ae513
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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