Hydrochloric Acid → HCID 89443805, compound

HRID 1771720Notes

Reaction equation

HRID 1771720 reaction equation
Br[C:2]1[C:3]([CH3:12])=[C:4]([C:8]([F:11])=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[F:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C([O-])([O-])=O.[Na+].[Na+].Cl>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>[F:11][C:8]1[C:4]([C:5]([OH:7])=[O:6])=[C:3]([CH3:12])[C:2]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([F:13])[CH:19]=2)=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 847957933-Bromo-6-fluoro-2-methyl-benzoic acid

Product 1

HCID 89443805HCID 89443805, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 3-bromo-6-fluoro-2-methylbenzoic acid (1.35 g, 5.8 mmol, 1.0 eq) and 3-fluorophenyl boronic acid (970 mg, 6.9 mmol, 1.2 eq) in DMF (25 mL) under N2 were added Na2CO3 (2.45 g, 23.1 mmol, 4 eq) and Pd(PPh3)4 (0.33 g, 0.29 mmol, 0.05 eq). The reaction was heated at 95° C. overnight, then the reaction acidified by addition of 4M HCl to a final pH of 4. The reaction mixture was filtered through celite and extracted with EtOAc. The organic extract was washed with brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound (680 mg, 48%). This material was used without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-f7c643b66f984e62bd8a24295ecf9ec3
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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