Water → HCID 136059567, compound

HRID 499963Notes

Reaction equation

HRID 499963 reaction equation
C[O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][C:6]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:5][C:4]=1[C:19]1[N:24]=[C:23]([CH:25]=[O:26])[CH:22]=[CH:21][CH:20]=1.B(Br)(Br)Br.O.C([O-])([O-])=O.[Na+].[Na+]>ClCCl>[OH:2][C:3]1[C:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:7][C:6]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:5][C:4]=1[C:19]1[N:24]=[C:23]([CH:25]=[O:26])[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 59422052HCID 59422052, compound

Product 1

HCID 136059567HCID 136059567, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-80 °C

Procedure

In the glovebox, 6-(2′-methoxy-3′-phenyl-5′-tert-butylphenyl)-2-formyl-pyridine (11) (4.43 g, 12.3 mmol) was dissolved in 75 mL dichloromethane and cooled to −80° C. A 20 mL dichloromethane solution of BBr3 (4.62 g, 18.5 mmol) was slowly added dropwise and the solution was left to stir at −80° C. for 1 h. After warming to room temperature, the orange solution was taken out of the glovebox and under a purge of nitrogen, ˜1 mL of water was added, causing a large amount of smoke to form. A further 5 mL of water was slowly added, followed by 30 mL of dichloromethane and another 10 mL portion of water. This was stirred for 30 minutes, neutralized with 1M Na2CO3 and the water layer separated from the organic layer. The water layer was extracted with 2×75 mL dichloromethane, the organic layers combined and washed with water (2×100 mL), dried over MgSO4, filtered and dried to give compound 12 as a yellow solid. Yield: 4.25 g (100%).

Workup

  1. waitthe solution was left
  2. temperatureAfter warming to room temperature
  3. customunder a purge of nitrogen, ˜1 mL of water
  4. additionwas added
  5. customto form
  6. stirringThis was stirred for 30 minutes
  7. customthe water layer separated from the organic layer
  8. extractionThe water layer was extracted with 2×75 mL dichloromethane
  9. washwashed with water (2×100 mL)
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-a90dfa85fe2b4636aa0a57539ed08f46
Source dataset
uspto-grants-2010_08
Patent number
US07767773B2

Reaction notes

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