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Cesium carbonate → Methyl 2-bromo-2',6'-dimethoxybiphenyl-4-carboxylate

HRID 1040353
Notes
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Reaction equation

HRID 1040353 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1I)[C:5]([O:7][CH3:8])=[O:6].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[C:16]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.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>[Br:1][C:2]1[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=[CH:10][C:11]=1[C:16]1[C:15]([O:14][CH3:13])=[CH:20][CH:19]=[CH:18][C:17]=1[O:21][CH3:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2734343(2,6-Dimethoxyphenyl)boronic acidHCID 17750019Methyl 3-bromo-4-iodobenzoate

Product 1

HCID 66721235Methyl 2-bromo-2',6'-dimethoxybiphenyl-4-carboxylateYield 56%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

Stir a solution of 4.84 g (14.2 mmol) of methyl 3-bromo-4-iodobenzoate (J. Med. Chem., 1999, 42, 4088) and 3.88 g (21.29 mmol) of 2,6-dimethoxyphenyl boronic acid in 120 mL of DMF and 14.2 mL of a 2M aqueous solution of caesium carbonate for 15 minutes under argon, then add 984 mg (0.85 mmol) of Pd(PPh3)4 and heat for 2.5 h at 85° C. After concentration under reduced pressure, distribute the residue obtained in 600 mL of a 1:1 DCM/water mixture. Wash the organic phase with 100 mL of water, dry over MgSO4 and concentrate at reduced pressure. Purify the residue obtained by silica gel column chromatography, eluting with a heptane/EtOAc gradient from 0 to 10% of EtOAc. After concentration under reduced pressure, we obtain 2.79 g of methyl 2-bromo-2′,6′-dimethoxybiphenyl-4-carboxylate in the form of oil.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customobtained in 600 mL of a 1:1 DCM/water mixture
  3. washWash the organic phase with 100 mL of water
  4. dry with materialdry over MgSO4
  5. concentrationconcentrate at reduced pressure
  6. customPurify the residue
  7. customobtained by silica gel column chromatography
  8. washeluting with a heptane/EtOAc gradient from 0 to 10% of EtOAc
  9. concentrationAfter concentration under reduced pressure, we

Sources & evidence

ORD record
ord-28de07a469ee418a9fe2221d0b7db679
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08552201B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes