Sodium Carbonate → HCID 18474515, compound

HRID 2227989Notes

Reaction equation

HRID 2227989 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])(=O)=O.C([O-])([O-])=O.[Na+].[Na+].[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Li+].[Cl-]>C1(C)C=CC=CC=1.C1COCC1.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>[CH3:17][C:15]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:16]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 433294Lithium ChlorideHCID 18474576Methyl 2-trifluoromethylsulfonyloxy-4-methylbenzoate

Product 1

HCID 18474515HCID 18474515, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of product from step B (14 g; 47 mmol), 2M Na2CO3 (61.1 ml; 122.2 mmol) phenylboronic acid (6.3 g; 51.7 mmole) and LiCl (3.98 g; 94 mmol) in toluene (400 ml), was added, under argon atmosphere, a solution of tetrakis(triphenylphosphine)palladium (1.01 ml; 1.88 mmol) in THF (150 ml). The mixture was refluxed overnight, washed with 2N, NaOH and saturated NaCl. The organic phase was evaporated and the residue purified by flash chromatography (AcOEt/Petroleum ether: 95/5) to give methyl 4-methyl-2-phenylbenzoate as an oil (10.44 g; 98%).

Workup

  1. additionwas added, under argon atmosphere
  2. temperatureThe mixture was refluxed overnight
  3. washwashed with 2N, NaOH and saturated NaCl
  4. customThe organic phase was evaporated
  5. customthe residue purified by flash chromatography (AcOEt/Petroleum ether: 95/5)

Sources & evidence

ORD record
ord-586e54de0f30471f83ae8473692d2897
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

Loading…