Boron tribromide → HCID 18456631, compound

HRID 1272064Notes

Reaction equation

HRID 1272064 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:14])[C:10]([NH:12][CH3:13])=[O:11])=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:14])[C:10]([NH:12][CH3:13])=[O:11])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21776239HCID 21776239, compound

Product 1

HCID 18456631HCID 18456631, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(4-methoxy-phenyl)-N-methyl-2-oxo-acetamide (74a) (1.35 g, 6.99 mmol) in 25 mL of CH2Cl2 was added 1.0 M BBr3 in CH2Cl2 (14 mL, 28.0 mmol) at 0° C. The mixture was stirred at 0° C. to room temperature for two hours. The reaction was quenched with MeOH, neutralized with concentrated aqueous NH4OH to pH ˜7. The resulting mixture was stirred at room temperature for one hour. Water was added, and the mixture was extracted with CH2Cl2. The organic phase was dried over Na2SO4, concentrated, and purified by flash column chromatography eluting with 1:1 EtOAc and hexanes to provide 0.53 g off-white solid as the intermediate 74b. 1H NMR (300 MHz, CD3OD) δ 7.03 (d, 2H, J=8.86 Hz), 6.75 (d, 2H, J=8.86 Hz), 2.76 (s, 3H). LCMS (ESI+) [M+Na]/z Calc'd 202, found 202.

Workup

  1. customThe reaction was quenched with MeOH, neutralized with concentrated aqueous NH4OH to pH ˜7
  2. stirringThe resulting mixture was stirred at room temperature for one hour
  3. additionWater was added
  4. extractionthe mixture was extracted with CH2Cl2
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by flash column chromatography
  8. washeluting with 1:1 EtOAc and hexanes

Sources & evidence

ORD record
ord-35010ce1e304411aa7a01652e4d6e07e
Source dataset
uspto-grants-2007_04
Patent number
US07208500B2

Reaction notes

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