2-Chlorobenzaldehyde → HCID 69153642, compound

HRID 2251955Notes

Reaction equation

HRID 2251955 reaction equation
[Li]CCCC.C(NC(C)C)(C)C.[Br:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.[Cl:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=[O:24].[NH4+].[Cl-]>C1COCC1>[Br:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[CH:23]([C:22]1[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=1[Cl:20])[OH:24]

Participants

7

Reactant 5

HCID 69962-ChlorobenzaldehydeHCID 7912DiisopropylamineHCID 122863-BromopyridineHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 69153642HCID 69153642, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

Add n-BuLi (48.2 mL, 77.1 mmol, 1.6N in hexane) to a −70° C. solution of diisopropylamine (10.8 mL, 77.1 mmol) in THF (130 mL) in a flame-dried flask. After 30 minutes add 3-bromo-pyridine (2.48 mL, 25.7 mmol) dropwise and stir the mixture at −70° C. After 4 hours, add 2-chloro-benzaldehyde (2.95 mL, 26.2 mmol) dropwise, stir at −70° C. After 1 hour, warm reaction to RT, quench reaction with dropwise addition of 60 mL saturated NH4Cl solution. Extract with Et2O (3×), wash with brine, dry the combined organic layers over MgSO4 and concentrate. Purify the residue by flash chromatography on silica gel eluting with 0-40% EtOAc/hexane to afford the title compound: MS(IS) 299 (M+1); TLC (50% EtOAc/hexanes) Rf=0.23.

Workup

  1. stirringstir at −70° C
  2. waitAfter 1 hour
  3. temperaturewarm
  4. customreaction to RT
  5. customquench
  6. customreaction
  7. extractionExtract with Et2O (3×)
  8. washwash with brine
  9. dry with materialdry the combined organic layers over MgSO4
  10. concentrationconcentrate
  11. customPurify the residue by flash chromatography on silica gel eluting with 0-40% EtOAc/hexane

Sources & evidence

ORD record
ord-6544fcc6b8db4614b74856ff313c8981
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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