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

HRID 1455966ノート

反応式

HRID 1455966 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-7aa99d7866d14afb8e8d97e262d8670f
出典データセット
uspto-grants-1998_12
特許番号
US05843942

反応ノート

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