4-Bromo-3-methylbenzoyl chloride → HCID 21467212, compound

HRID 1939225Notes

Reaction equation

HRID 1939225 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([C:18](OC(C)(C)C)=O)[CH2:14][CH2:13]1)[NH:8][CH2:7][CH2:6]2.CC(C)([O-])C.[K+].[Br:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][C:33]=1[CH3:41]>C1COCC1>[Br:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:11]([N:12]4[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]4)[CH:10]=3)[CH:6]=[CH:7]2)=[O:37])=[CH:34][C:33]=1[CH3:41]

Participants

5

Reactant 3

HCID 70215344-Bromo-3-methylbenzoyl chlorideHCID 21467214HCID 21467214, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21467212HCID 21467212, compoundYield 15.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of intermediate 2 (0.25 g, 1.0 mmol) and potassium t-butoxide (0.114 g, 1 mmol) in dry THF (15 ml) was added 4-bromo-3-methyl benzoyl chloride (0.238 g, 1.0 mmol) in dry THF (10 ml). The resulting mixture was stirred at room temperature for 72 h, then poured onto water and extracted with dichloromethane (3×). The organic layers were combined, dried (Na2SO4), filtered and concentrated in vacuo to give the crude product Purification by Fcc eluting with 3% methanol/dichloromethane gave the title compound as a pale yellow oil (70 mg, 15%).

Workup

  1. additionpoured onto water
  2. extractionextracted with dichloromethane (3×)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give
  7. customthe crude product Purification by Fcc
  8. washeluting with 3% methanol/dichloromethane

Sources & evidence

ORD record
ord-80bb414b47aa4153851223e8c73013d7
Source dataset
uspto-grants-1997_12
Patent number
US05696122

Reaction notes

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