Triphenylphosphine → 4-(Bromomethyl)picolinonitrile

HRID 619855ノート

反応式

HRID 619855 の反応式
[Br:1]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:22]([C:24]1[CH:29]=[C:28]([CH2:30]O)[CH:27]=[CH:26][N:25]=1)#[N:23]>C(Cl)Cl>[C:22]([C:24]1[CH:29]=[C:28]([CH2:30][Br:1])[CH:27]=[CH:26][N:25]=1)#[N:23]

参加物

5

反応物 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 107253914-(Hydroxymethyl)pyridine-2-carbonitrile

生成物 1

HCID 106317764-(Bromomethyl)picolinonitrile収率 90.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Bromine (6.88 g, 43.1 mmol) is added dropwise to a solution of triphenylphosphine (11.3 g, 43.1 mmol) in 280 mL of CH2Cl2 at 0° C. The mixture is tirred for 30 minutes at 0° C. At this time, 2-cyano-4-(hydroxymethyl)-pyridine (4.82 g, 35.9 mmol) is added and the resulting mixture is stirred for 2 hours at room temperature. The reaction mixture is diluted with CH2Cl2 and washed with water (2x) and saturated NaCl solution. The organic layer is dried with MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting in a gradient of 20% EtOAc/hexanes to 30% EtOAc/hexanes to afford the title compound (6.40 g, 32.5 mmol) as an oil.

後処理

  1. washwashed with water (2x) and saturated NaCl solution
  2. dry with materialThe organic layer is dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by column chromatography
  6. washeluting in a gradient of 20% EtOAc/hexanes to 30% EtOAc/hexanes

出典と根拠

ORDレコード
ord-2588eef75cfc4e2e94f71ede74c68103
出典データセット
uspto-grants-1999_09
特許番号
US05958918

反応ノート

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