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

HRID 1455966노트

반응식

HRID 1455966 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-7aa99d7866d14afb8e8d97e262d8670f
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05843942

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