Carbon tetrabromide → 2-(Bromomethyl)-5-nitrothiophene

HRID 363510노트

반응식

HRID 363510 반응식
O[CH2:2][C:3]1[S:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:31]>ClCCl.[Cl-].[Na+].O>[Br:31][CH2:2][C:3]1[S:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 332588(5-nitrothiophen-2-yl)methanol

생성물 1

HCID 536851562-(Bromomethyl)-5-nitrothiophene수율 72.5%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

실험 절차

To a stirred solution of 2-hydroxymethyl-5-nitro-thiophene (18.8 g, 118 mmol) in dichloromethane (500 ml) at 0° C. was added triphenylphosphine (3 1.5 g, 120 mmol) followed by carbon tetrabromide (39 g, 118 mmol). The mixture was stirred for 2 hours, poured into half saturated brine and extracted with dichloromethane. The organic layer was dried over magnesium sulphate and the solvent removed at reduced pressure. The crude product was purified by silica gel chromatography using 15% ethyl acetate/hexane as the eluant to give 2-bromomethyl-5-nitrothiophene (19 g, 61%) as a brown oil.

후처리

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over magnesium sulphate
  3. customthe solvent removed at reduced pressure
  4. customThe crude product was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-3338c9d0cca2472dbb0af75964cf6133
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05874472

반응 노트

불러오는 중…