Sodium Carbonate → HCID 67286921, compound

HRID 403304Notes

Reaction equation

HRID 403304 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Br)=[CH:6][CH:5]=1.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[C:19]([CH:18]=[CH:17][CH:16]=1)[CH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:12])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 27343883-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 67286921HCID 67286921, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-bromomethyl-benzoic acid methyl ester 17h (1 g, 4.37 mmol), 3-trifluoromethylphenylboronic acid 15b (1 g, 5.25 mmol) and Pd(PPh3)4 (50 mg, 0.044 mmol) in dioxane (15 mL) was stirred at room temperature for 1 min. An aqueous solution of Na2CO3 (2M, 4 mL) was added. The resulting solution was heated at 90° C. for 5 h and was then cooled to room temperature. The reaction was partitioned between EtOAc and water. The organic phase was concentrated and purified by flash column chromatography (silica gel, 5% EtOAc/hexanes) to give compound 17i.

Workup

  1. temperatureThe resulting solution was heated at 90° C. for 5 h
  2. temperaturewas then cooled to room temperature
  3. customThe reaction was partitioned between EtOAc and water
  4. concentrationThe organic phase was concentrated
  5. custompurified by flash column chromatography (silica gel, 5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8f57c7dab5094fcc92e19a7f626000e7
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Reaction notes

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