Dimethylformamide → 2-Bromo-6-fluorobenzaldehyde

HRID 606299Notes

Reaction equation

HRID 606299 reaction equation
[Li]CCCC.CC1(C)CCCC(C)(C)N1.[Br:16][C:17]1[CH:18]=[C:19]([F:23])[CH:20]=[CH:21][CH:22]=1.CN([CH:27]=[O:28])C>C1COCC1>[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=1[CH:27]=[O:28]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 130352,2,6,6-TetramethylpiperidineHCID 140821-Bromo-3-fluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 224739772-Bromo-6-fluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of n-BuLi (25 mL of 1.6 M solution in hexane, 40 mmol) in THF (100 mL) is added 2,2,6,6-teramethylpiperidine (6.8 mL, 40 mmol) at −78° C. and the mixture is stirred for 20 minutes. To this is added 3-bromofluorobenzene (7.0 g, 40 mmol). After stirring for 3 hours at −78° C., DMF (15 mL, 200 mmol) is added and the mixture is warmed to room temperature and stirred for 1 hour. The mixture is quenched with 1N HCl and extracted with EtOAc. The combined extracts are dried (MgSO4) and concentrated in vacuo. The residue is purified by flash chromatography (elution with Hex/EtOAc 10:1) to yield 2-bromo-6-fluoro-benzaldehyde. 1H NMR (CDCl3) 10.4 (s, 1H), 7.48-7.39 (m, 2H), 7.18-7.14 (m, 1H).

Workup

  1. stirringAfter stirring for 3 hours at −78° C.
  2. stirringstirred for 1 hour
  3. customThe mixture is quenched with 1N HCl
  4. extractionextracted with EtOAc
  5. dry with materialThe combined extracts are dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash chromatography (elution with Hex/EtOAc 10:1)

Sources & evidence

ORD record
ord-c65a1766bb8f46aeab20e14f8d81ac2e
Source dataset
uspto-grants-2011_03
Patent number
US07915288B2

Reaction notes

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