Hydrochloric Acid → HCID 68659330, compound

HRID 1428926Notes

Reaction equation

HRID 1428926 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Li]CCCC.[F:18][C:19]1[CH:20]=[C:21]([CH:28]=[CH:29][CH:30]=1)[C:22](N(OC)C)=[O:23].Cl>C1COCC1.O>[F:18][C:19]1[CH:20]=[C:21]([CH:28]=[CH:29][CH:30]=1)[C:22]([C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])=[O:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 899062-Bromo-5-methoxybenzoic acidHCID 212657573-Fluoro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 68659330HCID 68659330, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A −78° C. solution of 2-bromo-5-methoxybenzoic acid (26.0 g, 112.5 mmol) in THF (100 mL) was treated with n-BuLi (1.6 M in hexane) (140 mL, 225 mmol) and stirred at −78° C. for 1 h. 3-fluoro-N-methoxy-N-methylbenzamide (15.3 g, 83.8 mmol) in THF (40 mL) was added dropwise then warmed to rt for 16 h. The reaction mixture was diluted with water (100 mL), acidified with 5N HCl (25 mL) and extracted with EtOAc (3×200 mL). The organic layer was washed with brine, dried over Na2SO4, and concentrated to obtain 2-(3-fluorobenzoyl)-5-methoxybenzoic acid (21.0 g, 68%) (274.83 [M+H]); 1H NMR: (400 MHz, DMSO) δ: 3.89 (s, 3H), 7.26-7.29 (m, 1H), 7.37-7.45 (m, 4H), 7.50-7.55 (m, 2H).

Workup

  1. temperaturethen warmed to rt for 16 h
  2. extractionextracted with EtOAc (3×200 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f70f856412294fc8b0eb4f5ea96d96f0
Source dataset
uspto-grants-2015_01
Patent number
US08937178B2

Reaction notes

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