Diethyl Ether → HCID 57886825, compound

HRID 1818735Notes

Reaction equation

HRID 1818735 reaction equation
Br[C:2]1[C:3]([O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])=[N:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])=[N:6][CH:7]=1.C1[CH2:30][O:29]CC1.C([Mg]Cl)(C)C.C([O:38]CC)C>>[F:16][C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[O:8][C:5]1[N:4]=[C:3]([O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])[C:2]([C:30]([OH:29])=[O:38])=[CH:7][N:6]=1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 59834408HCID 59834408, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 57886825HCID 57886825, compound

Conditions

Temperature
0 °C

Procedure

5-Bromo-2,4-bis-(2,4-difluoro-phenoxy)-pyrimidine (1.0 g, 2.41 mmol) was added to 30 mL of a 1:1 mixture of dry THF and diethyl ether. The mixture was cooled to 0° C. in an ice bath, and isopropyl magnesium chloride (1.45 mL of 2 M solution in diethyl ether, 2.41 mmol) was added dropwise to the stirring mixture. The reaction mixture was stirred at 0° C. for on hour, then dry CO2 was bubbled through the stirring reaction mixture for 45 minutes. The reaction mixture was stirred under CO2 atmosphere for another 30 minutes, then was concentrated under reduced pressure. The residue was taken up into a mixture of 30 mL water and 5 mL THF, and the mixture was acidified to pH=2 by dropwise addition of 10% aqueous HCl. The mixture was extracted wtih EtOAc and the organic layer was washed with water, dried (MgSO4), filtered and concentrated under reduced pressure to give 950 mg of 2,4-bis-(2,4-difluoro-phenoxy)-pyrimidine-5-carboxylic acid. MS(M+H)=381.

Workup

  1. customdry CO2 was bubbled through the stirring reaction mixture for 45 minutes
  2. stirringThe reaction mixture was stirred under CO2 atmosphere for another 30 minutes
  3. concentrationwas concentrated under reduced pressure
  4. additionThe residue was taken up into a mixture of 30 mL water and 5 mL THF
  5. additionthe mixture was acidified to pH=2 by dropwise addition of 10% aqueous HCl
  6. extractionThe mixture was extracted wtih EtOAc
  7. washthe organic layer was washed with water
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b7491aed33654d138a154e780ae7c368
Source dataset
uspto-grants-2009_10
Patent number
US07601726B2

Reaction notes

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