Water → 2-fluoro-5-phenylbenzoic acid

HRID 659122Notes

Reaction equation

HRID 659122 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>CC(OC)(C)C>[F:11][C:5]1[CH:4]=[CH:3][C:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 66827Phenylboronic AcidHCID 27363155-Bromo-2-fluorobenzoic acid

Product 1

HCID 117460232-fluoro-5-phenylbenzoic acid

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

5-Bromo-2-fluoro-benzoic acid (49) (2.0 g, 9.00 mmol) was coupled to phenyl boronic acid (1.23 g, 10.00 mmol) using method F, except that after the 2 hour reaction, water (50 mL) and TBME (50 mL) were added. The mixture was filtered and the aqueous layer was washed with TBME. The aqueous layer was then acidified with 1N HCl and the precipitated solid was collected and dried. Yield: 1.6 g, 82%

Workup

  1. additionwere added
  2. filtrationThe mixture was filtered
  3. washthe aqueous layer was washed with TBME
  4. customthe precipitated solid was collected
  5. customdried

Sources & evidence

ORD record
ord-dc6f96587ca14cf2b989a663a0902b97
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Reaction notes

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