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

HRID 572543Notes

Reaction equation

HRID 572543 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, (40 g; 154 mmol), o-tolylboronic acid (23 g; 170 mmol), K2CO3 (107 g; 772 mmol), tetrakis(triphenylphosphine)palladium (0) (1.8 g; 1.5 mmol) were taken up in toluene (200 mL) and water (200 mL) under N2 atmosphere. The reaction mixture was purged with vacuum, then degassed with N2 and then refluxed for 1 hour. The reaction mixture was cooled to RT, filtered over a pad of celite and washed with EtOAc (1 L). The filtrate was concentrated, affording 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 (42 g, quantitative). HPLC (Method A) Rt 5.34 min (Purity: 89.4%).

Workup

  1. customThe reaction mixture was purged with vacuum
  2. customdegassed with N2
  3. temperaturerefluxed for 1 hour
  4. filtrationfiltered over a pad of celite
  5. washwashed with EtOAc (1 L)
  6. concentrationThe filtrate was concentrated
  7. customaffording 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-f8a7ac5b189f435a9fefb4ee7e25efd0
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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