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Sodium Carbonate → Methyl 3-bromo-5-(4-fluorophenyl)benzoate

HRID 1726384
Notes
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Reaction equation

HRID 1726384 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[F:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOCCOC.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([C:17]2[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:3]=[C:4]([CH:9]=[C:10]([C:17]3[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=3)[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[CH:16][CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 621923Methyl 3,5-Dibromobenzoate

Product 2

HCID 69062042Methyl 3,5-di(4-fluorophenyl)benzoateYield 4%HCID 69068418Methyl 3-bromo-5-(4-fluorophenyl)benzoateYield 23%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst
HCID 702EthanolSolvent
HCID 8150DiglymeSolvent

Conditions

Temperature
88 °C

Procedure

To a solution of methyl 3,5-dibromobenzoate (3.00 g, 10.2 mmol) and 4-fluoro-phenyl boronic acid (1.43 g, 10.2 mmol) in 2-methoxyethyl ether (60 ml) and ethanol (3 ml) was added Na2CO3 (saturated, 9 ml), followed by tetrakis(triphenylphosphine) palladium (0) (0.2 g). The mixture was heated at 88° C. for 1.5 h, then cooled to room temperature, partitioned between hexane and water, and the organic phase washed with brine, dried over anhydrous sodium sulfate, decanted, and the organic solution concentrated under reduced pressure. The residue was purified by silica gel chromatography (1% EtOAc in hexane) to yield methyl 3-bromo-5-(4-fluorophenyl)benzoate (intermediate XXXIVa, 0.725 g, 23%) as a white solid, and methyl 3,5-di(4-fluorophenyl)benzoate (intermediate XXXIVb, 0.128 g, 4%) as a white solid.

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between hexane and water
  3. washthe organic phase washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customdecanted
  6. concentrationthe organic solution concentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (1% EtOAc in hexane)

Sources & evidence

ORD record
ord-f7d2824e37d748efbaa5e49b5eac6485
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07491821B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes