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

HRID 363510ノート

反応式

HRID 363510 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 536851562-(Bromomethyl)-5-nitrothiophene収率 72.5%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3338c9d0cca2472dbb0af75964cf6133
出典データセット
uspto-grants-1999_02
特許番号
US05874472

反応ノート

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