Sodium Acetate → 2,6-Dibromobenzyl acetate

HRID 1186068Notes

Reaction equation

HRID 1186068 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH2:9]Br.[CH3:11][C:12]([O-:14])=[O:13].[Na+]>CN(C)C=O>[C:12]([O:14][CH2:9][C:3]1[C:4]([Br:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])(=[O:13])[CH3:11]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 133810151,3-Dibromo-2-(bromomethyl)benzene

Product 1

HCID 592164132,6-Dibromobenzyl acetateYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1,3-dibromo-2-(bromomethyl)benzene (27.6 g, 84 mmol), NaOAc (35.5 g, 5 eq.) and dimethylformamide (DMF) (150 mL) was stirred at 100° C. (hot oil bath temperature) for 1.75 h, allowed to cool, and then partitioned between heptane (500 mL) and water (200 mL). After removing the organic layer, the aqueous layer was extracted with heptane (200 mL). The combined organics were washed with H2O (2×300 mL), dried (Na2SO4), filtered, and evaporated to give 24.57 g (yield of 95%) of title product as a colorless oil. This oil contained 13% unreacted starting material but was successfully used without further purification. 1H NMR (300 MHz, CDCl3) δ 2.10 (s, 3H), 5.41 (s, 2H), 7.08 (t, 1H), 7.58 (d, 2H).

Workup

  1. temperatureto cool
  2. custompartitioned between heptane (500 mL) and water (200 mL)
  3. customAfter removing the organic layer
  4. extractionthe aqueous layer was extracted with heptane (200 mL)
  5. washThe combined organics were washed with H2O (2×300 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-3cd4cf0e8b954dd1a20b1e820422cc88
Source dataset
uspto-grants-2014_03
Patent number
US08673897B2

Reaction notes

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