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

HRID 356977노트

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HRID 356977 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 222277664-(Bromomethyl)-3,5-dichloropyridine수율 73.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-32da9f33367940dda99b4480a5b4cecf
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840724

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