Water → 6-Bromo-2-fluoro-3-methoxybenzaldehyde

HRID 1987140Notes

Reaction equation

HRID 1987140 reaction equation
[Li+].CC([N-]C(C)C)C.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([F:18])[CH:11]=1.CN([CH:22]=[O:23])C.O>C1COCC1>[Br:9][C:10]1[C:11]([CH:22]=[O:23])=[C:12]([F:18])[C:13]([O:16][CH3:17])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 753784-Bromo-2-fluoroanisoleHCID 2724682Lithium diisopropylamide

Product 1

HCID 231579156-Bromo-2-fluoro-3-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred solution of LDA (62 mmol) in THF (100 mL) was added 4-bromo-2-fluoro-1-methoxybenzene (12 g, 59 mmol) in THF (20 mL) slowly at −78° C. The reaction mixture was left to stir at −78 C for 2 h, treated with DMF (15 g, 210 mmol) in THF (20 mL) slowly, left to stir at −78 C for 1 h, and allowed to warm to room temperature as the bath did. The reaction mixture was treated with water and extracted with EtOAc (×3). The combined organics were washed with brine, dried (Na2SO4), concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (600 MHz, CDCl3) δ 10.34 (s, 1H); 7.39 (dd, 1H); 7.04 (t, 1H); 3.92 (s, 3H).

Workup

  1. waitThe reaction mixture was left
  2. waitleft
  3. stirringto stir at −78 C for 1 h
  4. extractionextracted with EtOAc (×3)
  5. washThe combined organics were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-bf01ffc0f68041288f8db2e5f3449595
Source dataset
uspto-grants-2009_06
Patent number
US07550478B2

Reaction notes

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