Sodium Carbonate → 5-Ethyl-2-fluoro-biphenyl

HRID 2105032Notes

Reaction equation

HRID 2105032 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[CH:5]=[CH:4][C:3]=1[F:10].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.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>[CH2:8]([C:6]1[CH:5]=[CH:4][C:3]([F:10])=[C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=1)[CH3:9]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 187118742-Bromo-4-ethyl-1-fluorobenzene

Product 1

HCID 214329185-Ethyl-2-fluoro-biphenyl

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
150 °C

Procedure

To a degassed mixture of Intermediate 228.1 (104 mg, 0.512 mmol), phenylboronic acid (94 mg, 0.768 mmol) and Na2CO3 (217 mg, 2.05 mmol) in 4 mL DME/H2O (3:1) was added Pd(PPh3)4 (59 mg, 0.051 mmol). The mixture was stirred at 150° C. for 5 min in a microwave oven, then was diluted with EtOAc, washed with water and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (100% hexanes) to afford Intermediate 228.2.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography (100% hexanes)

Sources & evidence

ORD record
ord-f0ecc30fe858434dbd837f304c614d5a
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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