Triphenylphosphine → Methyl 5-bromo-2-(2-thienylmethoxy)benzoate

HRID 1455966Notes

Reaction equation

HRID 1455966 reaction equation
[Br:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]([OH:12])=[CH:4][CH:3]=1.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:18][C:14]2[S:13][CH:17]=[CH:16][CH:15]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 694672-ThiophenemethanolHCID 77683Methyl 5-bromosalicylateHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 22105630Methyl 5-bromo-2-(2-thienylmethoxy)benzoateYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 5-bromosalicylate [prepared by treating methyl 5-bromosalicyclic acid with methanol and sulphuric acid] (4.62 g, 20 mmol) was dissolved in THF (150 mL) and treated with thiophene methanol (2.28 g, 20 mmol) and triphenyl phosphine (10.4 g, 40 mmol). The reaction was cooled in an ice bath and treated with DEAD (6.96 g, 20 mmol). The resultant orange solution was allowed to stir at ambient temperature under argon for 18 hours. The reaction mixture was evaporated and the residue subjected to chromatography (eluant: diethyl ether/hexane) to give methyl 5-bromo-2-(2-thienylmethoxy)benzoate as a pink oil (3.6 g, 55%).

Workup

  1. temperatureThe reaction was cooled in an ice bath
  2. customThe reaction mixture was evaporated

Sources & evidence

ORD record
ord-7aa99d7866d14afb8e8d97e262d8670f
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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