Ethyl Acetate → HCID 12085901, compound

HRID 1860292Notes

Reaction equation

HRID 1860292 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[Si](C)(C)C)=[C:9](/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)\[CH2:10][CH3:11])=[CH:4][CH:3]=1.[Br:22]Br.C[O-].[Na+].CCOC(C)=O>C(Cl)Cl.CO>[Br:22]/[C:8](/[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[C:9](\[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)/[CH2:10][CH3:11]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24408BromineHCID 10942334Sodium MethoxideHCID 12085900HCID 12085900, compound

Product 1

HCID 12085901HCID 12085901, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2) (3.93 g, 13.2 mmol) in CH2Cl2 (25 mL) at −78° C. was added bromine (2.5 g, 15.8 mmol) in 11 mL CH2Cl2 dropwise over 0.5 h. A solution of NaOMe (26.2 mmol) in methanol (36 mL) was added and the mixture was allowed to warm to rt. After stirring 3.5 h, EtOAc was added and the solution was washed with water, brine, and was dried (MgSO4) . The solvent was removed under reduced pressure and the resulting solid was recrystallized (methanol) to give the bromide (3) as a white solid (2.36 g, 59%): 1 H NMR (CDCl3) δ 7.33 (m, 7 H), 7.08 (m, 2 H), 2.33 (q, J=7.7 Hz, 2 H), 0.86 (t, J=7.7 Hz, 3 H).

Workup

  1. washthe solution was washed with water, brine
  2. dry with materialwas dried (MgSO4)
  3. customThe solvent was removed under reduced pressure
  4. customthe resulting solid was recrystallized (methanol)

Sources & evidence

ORD record
ord-3ff04f024f7e470f913f10a451b073c7
Source dataset
uspto-grants-2003_03
Patent number
US06528681B2

Reaction notes

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