Hydrochloric Acid → Benzyl 3-fluoro-4-formylbenzoate

HRID 2233059Notes

Reaction equation

HRID 2233059 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH:13]=[O:14])[C:7]([OH:9])=[O:8].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>CN(C)C=O>[CH2:15]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:12]([CH:13]=[O:14])=[C:4]([F:3])[CH:5]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 212845583-Fluoro-4-formylbenzoic acid

Product 1

HCID 59295103Benzyl 3-fluoro-4-formylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% NaH (0.23 mol) is added portionwise to a solution of 3-fluoro-4-formyl benzoic acid (3, 0.19 mol) in dry dimethylformamide (DMF) (570 mL). The mixture is stirred at room temperature for 45 min. Benzyl bromide (0.23 mol) is added dropwise to the mixture. After stirring at room temperature for 5 h, the reaction mixture is poured into 1N HCl (ca. 1000 mL) and extracted twice with EtOAc. The combined extracts are washed with saturated aqueous NaHCO3, brine, dried over MgSO4, and evaporated in vacuo to give crude 3-fluoro-4-formyl benzoic acid benzyl ester (6).

Workup

  1. stirringAfter stirring at room temperature for 5 h
  2. extractionextracted twice with EtOAc
  3. washThe combined extracts are washed with saturated aqueous NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-ba5eea9c5845426aa9e490824d32e897
Source dataset
uspto-grants-2010_05
Patent number
US07709470B2

Reaction notes

Loading…