Dimethylformamide → 2,6-Dibromobenzyl acetate

HRID 1918802Notes

Reaction equation

HRID 1918802 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH2:9]Br.[C:11]([O-:14])(=[O:13])[CH3:12].[K+].CN(C=O)C>O>[C:11]([O:14][CH2:9][C:3]1[C:4]([Br:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 517044Potassium AcetateHCID 133810151,3-Dibromo-2-(bromomethyl)benzene

Product 1

HCID 592164132,6-Dibromobenzyl acetateYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet was purged with nitrogen and charged with 1,3-dibromo-2-(bromomethyl)benzene (3.28 g, 10.0 mmol), potassium acetate (3.93 g, 40.0 mmol) and DMF (100 mL). The solution was stirred at room temperature for 14 h. After that time, the reaction mixture was diluted with water (900 mL) and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with brine (100 mL), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford an 88% yield (2.70 g) of 2,6-dibromobenzyl acetate 104g as an off-white solid: mp 62-65° C.; 1H NMR (300 MHz, CDCl3) d 7.57 (d, 2H, J=8.0 Hz), 7.07 (t, 1H, J=7.9 Hz), 5.42 (s, 2H), 2.11 (s, 3H); MS (ESI+)

Workup

  1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet
  2. customwas purged with nitrogen
  3. extractionextracted with ethyl acetate (3×200 mL)
  4. washThe combined organic layers were washed with brine (100 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4ad074be38d649f2afa2bfb646f5b109
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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