Sulfuric Acid → Methyl 3'-hydroxy-2,2'-dimethylbiphenyl-4-carboxylate

HRID 2307555Notes

Reaction equation

HRID 2307555 reaction equation
COC[O:4][C:5]1[C:6]([CH3:14])=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1.Br[C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=1[CH3:26].C(=O)([O-])[O-].[K+].[K+].S(=O)(=O)(O)O>COCCOC.CO.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)C.O>[OH:4][C:5]1[C:6]([CH3:14])=[C:7]([C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=2[CH3:26])[CH:8]=[CH:9][CH:10]=1

Participants

9

Reactant 4

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 3294148Methyl 4-bromo-3-methylbenzoateHCID 226069353-Methoxymethoxy-2-methylbenzene-1-boronic acid

Product 1

HCID 22606889Methyl 3'-hydroxy-2,2'-dimethylbiphenyl-4-carboxylate

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolventHCID 21584184Diethylether waterSolvent

Conditions

Temperature
80 °C

Procedure

1.03 g (5.2 mmol) of 3-methoxymethoxy-2-methylbenzene-1-boronic acid, 1 g (4.4 mmol) of methyl 4-bromo-3-methylbenzoate and 4.4 mL of 2.0M potassium carbonate solution are dissolved in 20 mL of ethylene glycol dimethyl ether. The mixture is degassed using a stream of nitrogen for 10 minutes, and 250 mg (0.22 mmol) of tetrakis(triphenylphosphine)palladium are then added and the medium is stirred for 24 hours at 80° C. After cooling and the usual treatment, the residue obtained is dissolved in 30 mL of methanol and 0.5 mL of sulphuric acid is added. The medium is stirred at room temperature for 6 hours and then poured into an ethyl ether/water mixture. After extraction with ether, the residue is purified by chromatography on silica gel (eluent: 9 heptane/1 ethyl acetate). The desired product is obtained in the form of a thick, colourless oil (m=890 mg; Y=79%).

Workup

  1. customThe mixture is degassed
  2. customfor 10 minutes
  3. temperatureAfter cooling
  4. customthe usual treatment, the residue obtained
  5. stirringThe medium is stirred at room temperature for 6 hours
  6. extractionAfter extraction with ether
  7. customthe residue is purified by chromatography on silica gel (eluent: 9 heptane/1 ethyl acetate)

Sources & evidence

ORD record
ord-272dd39cc4c44f76a70ca4c98183a909
Source dataset
uspto-grants-2004_12
Patent number
US06831106B1

Reaction notes

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