Acetic Acid → HCID 11747443, compound

HRID 1936561Notes

Reaction equation

HRID 1936561 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:11][CH3:12])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.C(O)(=O)C.[Br:17]Br>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:9][C:8]([C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[S:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 10965199HCID 10965199, compound

Product 1

HCID 11747443HCID 11747443, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a stirring solution of 20c (2.07 g, 11.34 mmol), carbon tetrachloride (62 ml) and glacial acetic acid (2.07 ml) was added at room temperature a solution of bromine (μL 546.6, 10.66 mmol) in carbon tetrachloride (34 ml). The first drop was added and after 20 minutes the solution was added dropwise in 4 hours. After stirring for 16 hours the solvent was distilled and to the residue was added water and solid sodium bicarbonate (to pH 7), the organic phase was separated and water extracted with dichloromethane (3×30 ml), the organic layers were dried and evaporated. The crude product was chromatographed (70% petroleum ether 40-60° in dichloromethane) to give 1.90 g of 21c as a yellowish solid (64% yield). 1H NMR (CDCl3) δ7.47-7.42 (dd, 1H, J=8.85, 2.84 Hz); 7.38-7.18(m, 2H); 4.42 (s, 2H); 2.43 (s, 3H).

Workup

  1. additionThe first drop was added and after 20 minutes the solution
  2. additionwas added dropwise in 4 hours
  3. distillationwas distilled and to the residue
  4. additionwas added water and solid sodium bicarbonate (to pH 7)
  5. customthe organic phase was separated
  6. extractionwater extracted with dichloromethane (3×30 ml)
  7. customthe organic layers were dried
  8. customevaporated
  9. customThe crude product was chromatographed (70% petroleum ether 40-60° in dichloromethane)

Sources & evidence

ORD record
ord-a2a4456937e44f53bfc89a0775c6c05a
Source dataset
uspto-grants-2002_05
Patent number
US06391870B2

Reaction notes

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