Diethyl Ether → HCID 18518531, compound

HRID 1477739Notes

Reaction equation

HRID 1477739 reaction equation
I[C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+].CCOCC>C1(C)C=CC=CC=1.CCO.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>[CH3:12][C:9]1[CH:8]=[C:3]([C:4]([O:6][CH3:7])=[O:5])[C:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 14263946Benzoic acid, 2-iodo-5-methyl-, methyl ester

Product 1

HCID 18518531HCID 18518531, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Pd(PPh3)4 (523 mg, 0.45 mmol) was added to a rt solution of methyl 2-iodo-5-methylbenzoate in toluene (23 mL). After the solution was stirred for 10 min, a solution of phenylboronic acid (1.24 g, 9.96 mmol) in EtOH (10 mL) was added, followed by 2M aq. Na2CO3 (21 mL). The mixture was vigorously stirred and heated to reflux for 24 h. The rxn mixture was allowed to reach rt, then Et2O was added and the org. layer was separated and concentrated in vacuo. Purification by FC (Biotage SP1: EtOAc/hept eluting with a gradient of 0-10% EtOAc) was performed to give methyl 4-methyl-[1,1′-biphenyl]-2-carboxylate as a colorless oil. LC-MS A: tR=0.94 min; [M+H]+=227.16.

Workup

  1. stirringThe mixture was vigorously stirred
  2. temperatureheated
  3. temperatureto reflux for 24 h
  4. customto reach rt
  5. customlayer was separated
  6. concentrationconcentrated in vacuo
  7. customPurification by FC (Biotage SP1
  8. washEtOAc/hept eluting with a gradient of 0-10% EtOAc)

Sources & evidence

ORD record
ord-6900cf6b237347d7ad195f5dcc0940b3
Source dataset
uspto-grants-2016_08
Patent number
US09403813B2

Reaction notes

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