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

HRID 2247437Notes

Reaction equation

HRID 2247437 reaction equation
[CH2:1]([O:8][CH:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1([O:18][CH3:19])B(O)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C(O)C.C(=O)([O-])[O-].[K+].[K+].Br[C:32]1[CH:33]=[C:34]([CH2:38][C:39]([O:41][CH3:42])=[O:40])[CH:35]=[CH:36][CH:37]=1.Cl>C(OCC)C.COCCOC.[Pd].ClC1[C-](P)C(C2C=CC=CC=2)=C(C2C=CC=CC=2)C=1Cl.[CH-]1C=CC=C1.[Fe+2]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:36]2[CH:37]=[CH:32][CH:33]=[C:34]([CH2:38][C:39]([O:41][CH3:42])=[O:40])[CH:35]=2)[CH:12]=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 1030Propylene GlycolHCID 11430Potassium CarbonateHCID 11746402Methyl 2-(3-bromophenyl)acetateHCID 686332012-Benzyloxy-1-methoxybenzeneboronic acid

Product 1

HCID 59219255Methyl (3'-benzyloxy-4'-methoxybiphenyl-3-yl)acetateYield 55.5%

Reagents, catalysts & solvents 3

HCID 178527692HCID 178527692, compoundCatalystHCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

1.753 g of 2-Benzyloxy-1-methoxybenzeneboronic acid was suspended in 50 ml of diethyl ether, and 0.49 ml of propylene glycol was added thereto. The mixture was stirred at room temperature for 1 hour, and the solvent was removed to give 2-(3-benzyloxy-4-methoxyphenyl)-[1,3,2]dioxaborynane. This product was dissolved in 30 ml of 1,2-dimethoxyethane, then 1.5 g of potassium carbonate, 1.9 g of methyl 3-bromophenylacetate and 270 mg of dichlorodiphenyl phosphinoferrocene palladium were added thereto, and the mixture was stirred at 80° C. for 3 hours in a nitrogen atmosphere. The reaction mixture was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography, to give 1.356 g of the title compound in the 6:1→4:1 fraction.

Workup

  1. customthe solvent was removed
  2. customto give 2-(3-benzyloxy-4-methoxyphenyl)-[1,3,2]dioxaborynane
  3. stirringthe mixture was stirred at 80° C. for 3 hours in a nitrogen atmosphere
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1e524e2bacc5478e973d7ae9fb5b2da0
Source dataset
uspto-grants-2010_03
Patent number
US07687664B2

Reaction notes

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