Tetrahydrofuran → Ethyl 3-(4-bromo-2-methylphenyl)acrylate

HRID 1294380Notes

Reaction equation

HRID 1294380 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([CH3:10])[CH:3]=1.C[C:12]([CH3:15])([O-:14])C.[K+].C1C[O:20][CH2:19][CH2:18]1>>[Br:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:18]/[C:19]([O:14][CH2:12][CH3:15])=[O:20])=[C:4]([CH3:10])[CH:3]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 135551504-Bromo-2-methylbenzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 86598121Ethyl 3-(4-bromo-2-methylphenyl)acrylate

Procedure

To a solution of 4-bromo-2-methylbenzaldehyde (1 eq) and triethylphosphonoacetate (1.1 eq) in THF (0.3M) at rt was added dropwise potassium t-butoxide (1.1 eq, 1M, THF). The mixture was stirred at rt 3 h, quenched with HCl 10%, diluted with ether, washed with a NaHCO3 Solution, brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hexane:EtOAc; 90:10 to 70:30) afforded the title compound.

Workup

  1. customquenched with HCl 10%
  2. additiondiluted with ether
  3. washwashed with a NaHCO3 Solution, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b4f52b7b95a945029a9c3f048999b5f6
Source dataset
uspto-grants-2007_07
Patent number
US07238706B2

Reaction notes

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