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

HRID 2405199Notes

Reaction equation

HRID 2405199 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-286b2ed7a0d8468a9b591113a88512c7
Source dataset
uspto-grants-2014_08
Patent number
US08802720B2

Reaction notes

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