Water → Methyl 2'-(methoxymethyl)-2-methylbiphenyl-4-carboxylate

HRID 219832

Reaction equation

HRID 219832 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[CH3:12].[CH3:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=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>[CH3:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 3294148Methyl 4-bromo-3-methylbenzoateHCID 37594082-(Methoxymethyl)benzeneboronic acid

Product 1

HCID 67529166Methyl 2'-(methoxymethyl)-2-methylbiphenyl-4-carboxylate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-bromo-3-methylbenzoate (Aldrich 532878, 2 g; 8.73 mmol; 1 eq.), (2-methoxymethylphenyl)boronic acid (1.59 g; 9.60 mmol; 1.10 eq.), K2CO3 (6.03 g; 43.65 mmol; 5 eq.), tetrakis(triphenylphosphine)palladium (0) (1.01 g; 0.87 mmol; 0.10 eq.) were taken up in Toluene (10 mL) and water (10 mL) under N2 atmosphere. The reaction mixture was purged with vacuum, then degassed with N2 and then for 2 hours. The reaction mixture was cooled to RT, filtered over a pad of celite and washed with EtOAc (500 mL). The filtrate was concentrated to afford a yellow oil which was taken in EtOAc (100 mL). The organic layer was washed with a saturated aqueous solution of NaHCO3 solution (30 mL), water (30 mL) and brine (30 mL), dried over MgSO4 and concentrated affording the title compound as a brown oil used without further purification (3 g, quantitative). HPLC (Method A) Rt 5.20 min (Purity: 64.5%).

Workup

  1. customThe reaction mixture was purged with vacuum
  2. customdegassed with N2
  3. filtrationfiltered over a pad of celite
  4. washwashed with EtOAc (500 mL)
  5. concentrationThe filtrate was concentrated
  6. customto afford a yellow oil which
  7. washThe organic layer was washed with a saturated aqueous solution of NaHCO3 solution (30 mL), water (30 mL) and brine (30 mL)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-88765165c68946cfac2a9b5fd657a8bd
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Linked notes

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