Potassium Carbonate → HCID 57704854, compound

HRID 607102Notes

Reaction equation

HRID 607102 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1B1OC(C)(C)C(C)(C)O1.Br[C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][C:21]=1[F:30].C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].CCOC(C)=O>[F:30][C:21]1[CH:22]=[C:23]([C:24]([O:26][CH3:27])=[O:25])[CH:28]=[CH:29][C:20]=1[C:3]1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=1[F:1]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 17964843HCID 17964843, compoundHCID 21951878Methyl 4-bromo-3-fluorobenzoate

Product 1

HCID 57704854HCID 57704854, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-(2-fluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (600 mg, 2.38 mmol), methyl 4-bromo-3-fluorobenzoate (665 mg, 2.856 mmol), 1,1′-bis(diphenylphosphino) ferrocene-palladium dichloride dichloromethane adduct (292 mg, 0.358 mmol), potassium carbonate (2.38 ml, aq., 2M, 4.76 mmol) and 1,4-dioxane (10 ml) were sealed and subject to microwave irradiation at 145° C. for 15 min. Aliquot indicated formation of the desired cpd. TLC (20% EtOAc/hex) indicated a bright purple spot @ Rf=0.4. Crude mixture was dried/Na2SO4 then purified by flash chromatography (SiO2, Biotage 40+M cartridge). The column was eluted by a 0% to 20% EtOAc/hexanes mixture. Related fractions were pooled and concentrated in vacuo to afford the title compound. LCMS (ESI) calc.=278.08; found=279.09 (M+1)+.

Workup

  1. customirradiation at 145° C. for 15 min
  2. dry with materialCrude mixture was dried/Na2SO4
  3. customthen purified by flash chromatography (SiO2, Biotage 40+M cartridge)
  4. washThe column was eluted by a 0% to 20% EtOAc/hexanes mixture
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8ff15173f4a4b88989e2e1790c92cf1
Source dataset
uspto-grants-2011_03
Patent number
US07915271B2

Reaction notes

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