Water → Methyl 2-(methoxymethyl)-2'-methyl-[1,1'-biphenyl]-4-carboxylate

HRID 400741Notes

Reaction equation

HRID 400741 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][O:13][CH3:14].[C:15]1([CH3:24])[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C([O-])([O-])=O.[K+].[K+].O>C1(C)C=CC=CC=1.CCOC(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>[CH3:14][O:13][CH2:12][C:3]1[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:2]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH3:24]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 58554220Methyl 4-bromo-3-(methoxymethyl)benzoate

Product 1

HCID 58554139Methyl 2-(methoxymethyl)-2'-methyl-[1,1'-biphenyl]-4-carboxylate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-bromo-3-(methoxymethyl)benzoate obtained in step 2 (40 g; 154.38 mmol; 1 eq.), o-tolylboronic acid (23.09 g; 169.82 mmol; 1.10 eq.), K2CO3 (106.68 g; 771.90 mmol; 5 eq.), tetrakis(triphenylphosphine)palladium (0) (1.78 g; 1.54 mmol; 0.01 eq.) were taken up in toluene (200 mL) and water (200 mL) under nitrogen atmosphere. The reaction mixture was purged with vacuum, then degassed with nitrogen and then refluxed for 1 hour. The reaction mixture was cooled to room temperature, filtered over a pad of celite and washed with EtOAc (1000 mL). The filtrate was concentrated to afford a yellow oil which was taken in EtOAc (800 mL). The organic layer was washed with a saturated aqueous solution of NaHCO3 solution (250 mL), water (250 mL) and brine (250 mL), dried over MgSO4 and concentrated affording the title compound as a yellow oil used without further purification (41.9 g, quantitative). HPLC (Method A) Rt 5.34 min (Purity: 89.4%).

Workup

  1. customThe reaction mixture was purged with vacuum
  2. customdegassed with nitrogen
  3. temperaturerefluxed for 1 hour
  4. filtrationfiltered over a pad of celite
  5. washwashed with EtOAc (1000 mL)
  6. concentrationThe filtrate was concentrated
  7. customto afford a yellow oil which
  8. washThe organic layer was washed with a saturated aqueous solution of NaHCO3 solution (250 mL), water (250 mL) and brine (250 mL)
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-2bbc3a7927ce4f0f81d4caf9fb19d4b0
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

Loading…