Sodium Carbonate → HCID 67186699, compound

HRID 735870Notes

Reaction equation

HRID 735870 reaction equation
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[C:15]1([CH3:30])[CH:20]=[CH:19][C:18](C2C=CC=CC=2B(O)O)=[CH:17][CH:16]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.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>[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([C:18]2[CH:19]=[CH:20][C:15]([CH3:30])=[CH:16][CH:17]=2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 11334366Tert-butyl 4-bromobenzoateHCID 18181483HCID 18181483, compound

Product 1

HCID 67186699HCID 67186699, compoundYield 800%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of tert-butyl-4-bromobenzoate (48 g, 0.186 mol), 4-tolyl-benzeneboronic acid (25.3 g, 0.186 mol), Na2CO3 (200 g in 500 mL of water) in toluene (750 mL) under N2 was added Pd (PPh3)4 (10.7 g, 0.009 mol) and reaction mixture was refluxed for 10 h. After cooling to rt, organic layer was separated and aqueous layer was extracted with EtOAc (2×200 mL). The combined layer was washed with brine and concentrated. The crude was purified by column chromatography over silica gel (pet. ether/ethylacetate, 4:1) to give tert-butyl-4-(4-tolyl)benzoate (40 g, 800%) as a solid.

Workup

  1. temperaturewas refluxed for 10 h
  2. customorganic layer was separated
  3. extractionaqueous layer was extracted with EtOAc (2×200 mL)
  4. washThe combined layer was washed with brine
  5. concentrationconcentrated
  6. customThe crude was purified by column chromatography over silica gel (pet. ether/ethylacetate, 4:1)

Sources & evidence

ORD record
ord-3266be6b6bef44249b00d2a6e57beb1f
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

Loading…