Ethyl orthoformate → 2-Bromo-4-(diethoxymethyl)-1-fluorobenzene

HRID 1258009Notes

Reaction equation

HRID 1258009 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])C=O.[CH:11]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])OCC.[Br-].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>CCO>[Br:1][C:2]1[CH:3]=[C:4]([CH:11]([O:15][CH2:16][CH3:17])[O:18][CH2:19][CH3:20])[CH:7]=[CH:8][C:9]=1[F:10]

Participants

6

Reactant 4

HCID 31214Ethyl orthoformateHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 516892Sodium BicarbonateHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 131165852-Bromo-4-(diethoxymethyl)-1-fluorobenzeneYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 250 mL flask was charged with 3-bromo-4-fluorobenzaldehyde (13.5 g, 66.5 mmol), triethyl orthoformate (13.3 mL, 79.8 mmol), and anhydrous EtOH (150 mL). Tetrabutylammonium tribromide was added and the reaction mixture was allowed to stir at room temperature for 48 hours. The crude reaction was poured into aqueous NaHCO3 and extracted with ethyl acetate (75 ml). The organic layers were combined, dried with Na2SO4 and reduced under vacuum to afford the intermediate (16.2 g, 88%) as a clear oil. 1HNMR (CDCl3) δ ppm: 7.71 (1H), 7.40 (1H), 7.12 (1H), 5.48 (1H), 3.65-3.51 (4H), 1.28-1.24 (6H).

Workup

  1. customThe crude reaction
  2. extractionextracted with ethyl acetate (75 ml)
  3. dry with materialdried with Na2SO4

Sources & evidence

ORD record
ord-f22ef037af9c4dfdbb2d440d98760b1b
Source dataset
uspto-grants-2013_06
Patent number
US08466115B2

Reaction notes

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