Triphenylphosphine → 4-Bromo-3-(2-m-tolyl-ethoxy)-benzoic acid methyl ester

HRID 1810829Notes

Reaction equation

HRID 1810829 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[C:6]([OH:11])[CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:32][C:33]1[CH:34]=[C:35]([CH2:39][CH2:40]O)[CH:36]=[CH:37][CH:38]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[C:6]([O:11][CH2:40][CH2:39][C:35]2[CH:34]=[C:33]([CH3:32])[CH:38]=[CH:37][CH:36]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 746483-MethylbenzeneethanolHCID 5363146Diisopropyl azodicarboxylateHCID 6425184Methyl 4-Bromo-3-hydroxybenzoate

Product 1

HCID 670765654-Bromo-3-(2-m-tolyl-ethoxy)-benzoic acid methyl esterYield 102.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Bromo-3-hydroxy-benzoic acid methyl ester (1.00 g, 4.32 mmol) and triphenylphosphine (1.36 g, 5.19 mmol) were dissolved in THF. 2-(3-Methylphenyl)-ethanol (2-m-tolyl-ethanol) (0.707 g, 5.19 mmol) was added, the mixture was cooled in an ice bath, and DIAD (1.05 g, 5.19 mmol) was added slowly with stirring. The ice bath was removed and stirring continued overnight at room temperature. The volatiles were evaporated in vacuo, and the residue was purified by silica gel chromatography (HEP/EA gradient) to give 1.55 g of the title compound.

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. customThe ice bath was removed
  3. stirringstirring continued overnight at room temperature
  4. customThe volatiles were evaporated in vacuo
  5. customthe residue was purified by silica gel chromatography (HEP/EA gradient)

Sources & evidence

ORD record
ord-f16a651364fb41019a54260a452f8621
Source dataset
uspto-grants-2013_01
Patent number
US08362073B2

Reaction notes

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