Methanol → 4-(Bromomethyl)-3,5-dichloropyridine

HRID 356977ノート

反応式

HRID 356977 の反応式
O[CH2:2][C:3]1[C:8]([Cl:9])=[CH:7][N:6]=[CH:5][C:4]=1[Cl:10].[Br:11]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO>CN(C)C=O.O>[Br:11][CH2:2][C:3]1[C:8]([Cl:9])=[CH:7][N:6]=[CH:5][C:4]=1[Cl:10]

参加物

7

反応物 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 17855219(3,5-Dichloropyridin-4-yl)methanol

生成物 1

HCID 222277664-(Bromomethyl)-3,5-dichloropyridine収率 73.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

A cold (0° C.) solution of 4-hydroxymethyl-3,5-dichloropyridine (3.0 g) and N-bromosuccinimide (6.1 g) in dry dimethylformamide (100 mL) is treated with triphenylphosphine (8.9 g), portionwise, during 5 minutes. The resulting red solution is stirred at 0° C. for 45 minutes, and then treated with methanol (5 mL), followed by water (300 mL). The mixture is extracted with diethyl ether (4×200 mL), the combined organic washings dried over sodium sulfate, and the solvent removed under reduced pressure. The resulting residue is chromatographed on silica gel, eluting with a mixture of diethyl ether and pentane (1:2 v/v), to give 4-bromomethyl-3,5-dichloropyridine (3 g), in the form of an off-white solid, m.p. 40°-44° C.

後処理

  1. extractionThe mixture is extracted with diethyl ether (4×200 mL)
  2. dry with materialthe combined organic washings dried over sodium sulfate
  3. customthe solvent removed under reduced pressure
  4. customThe resulting residue is chromatographed on silica gel
  5. washeluting with a mixture of diethyl ether and pentane (1:2 v/v)

出典と根拠

ORDレコード
ord-32da9f33367940dda99b4480a5b4cecf
出典データセット
uspto-grants-1998_11
特許番号
US05840724

反応ノート

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