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Sodium Carbonate → 2,6-Dichloro-4-phenylbenzoic acid methyl ester

HRID 24720
Notes
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Reaction equation

HRID 24720 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[C:9]([Cl:10])=[CH:8][C:7](Br)=[CH:6][C:5]=1[Cl:12].[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.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>[CH3:1][O:2][C:3](=[O:13])[C:4]1[C:9]([Cl:10])=[CH:8][C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][C:5]=1[Cl:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 53951230Methyl 4-bromo-2,6-dichlorobenzoate

Product 1

HCID 538190002,6-Dichloro-4-phenylbenzoic acid methyl esterYield 104.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compound
Catalyst
HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,6-dichloro-4-bromobenzoic acid methyl ester (0.55 g) in THF (10 mL) was added benzeneboronic acid (1.30 g), Pd(PPh3)4 (0.16 g) and 2M Na2CO3 (5 mL). The mixture was refluxed for 4 h under N2. After cooling, the mixture was diluted with EtOAc and washed with water and brine. The organic layer was dried (Na2SO4), filtered, and concentrated. The residue was purified by preparative TLC (silica gel; eluent: hexane to EtOAc/hexane 1/1) to yield crude 2,6-dichloro-4-phenylbenzoic acid methyl ester (0.57 g). ESMS: m/z 281 (MH+).

Workup

  1. temperatureThe mixture was refluxed for 4 h under N2
  2. temperatureAfter cooling
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative TLC (silica gel; eluent: hexane to EtOAc/hexane 1/1)

Sources & evidence

ORD record
ord-0f0a43b938a345d99ae34da4537eebf9
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06855843B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes