Triphenylphosphine → 4-Bromo-3-[2-(2,4-dichlorophenyl)ethoxy]-5-hydroxybenzoic acid ethyl ester

HRID 433039Notes

Reaction equation

HRID 433039 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[CH2:28][CH2:29][OH:30].[CH2:31]([O:33][C:34](=[O:44])[C:35]1[CH:40]=[C:39](O)[C:38]([Br:42])=[C:37]([OH:43])[CH:36]=1)[CH3:32].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH2:31]([O:33][C:34](=[O:44])[C:35]1[CH:36]=[C:37]([OH:43])[C:38]([Br:42])=[C:39]([O:30][CH2:29][CH2:28][C:22]2[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:21]=2[Cl:20])[CH:40]=1)[CH3:32]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 27340992,4-Dichlorophenethyl alcoholHCID 5462977Diethyl azodicarboxylateHCID 57419684Ethyl 4-bromo-3,5-dihydroxybenzoate

Product 1

HCID 574196834-Bromo-3-[2-(2,4-dichlorophenyl)ethoxy]-5-hydroxybenzoic acid ethyl esterYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 17.8 g (67.9 mmol) of triphenylphosphane, 8.8 ml (67.9 mmol) of 2-(2,4-dichlorophenyl)ethanol and 16 g (61.3 mmol) of 4-bromo-3,5-dihydroxybenzoic acid ethyl ester in 25 ml of THF was added a solution of 10.6 ml (67.9 mmol) of DEAD in 40 ml of THF within 45 min between 6° and 18° C. After 16 h at room temperature the solvent was removed and the residue was stirred with cyclohexane/ethyl acetate (1/1) and filtered. The solid residue was stirred with cyclohexane and filtered. The remaining solid was separated by chromatography (cyclohexane/ethyl acetate (1/1)) to give 25.6 g (96%) of the title compound.

Workup

  1. customAfter 16 h at room temperature the solvent was removed
  2. filtrationfiltered
  3. stirringThe solid residue was stirred with cyclohexane
  4. filtrationfiltered
  5. customThe remaining solid was separated by chromatography (cyclohexane/ethyl acetate (1/1))

Sources & evidence

ORD record
ord-c9a4d78f4d4b430ca7b3896b705ff5c2
Source dataset
uspto-grants-2003_12
Patent number
US06664393B2

Reaction notes

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