Imidazole → 4-(2-Bromoethyl)-2-fluoro-1-methoxybenzene

HRID 1810015ノート

反応式

HRID 1810015 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[Br:25]Br.O[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([F:38])[CH:31]=1>C(Cl)Cl>[Br:25][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([F:38])[CH:31]=1

参加物

6

反応物 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 24408BromineHCID 27589993-Fluoro-4-methoxyphenethyl alcohol

生成物 1

HCID 534041114-(2-Bromoethyl)-2-fluoro-1-methoxybenzene収率 59.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of resin bound triphenyl phosphine (polystyrene 2% cross linking, loading=3 mmol/g, 3 g, 9 mmol) and imidazole (0.48 g, 7.1 mmol) in DCM (30 mL) cooled on an ice bath was drop wise added Br2 (1.13 g, 7.1 mmol), whereupon a solution of 4-(2-hydroxy-ethyl)-2-fluoro-1-methoxy-benzene (1.0 g, 5.88 mmol) in DCM (5 mL) was added. The cooling bath was removed and the reaction mixture was stirred for 16 hs before the resin was filtered off. The resin was washed with DCM and the filtrate was concentrated in vacuo. The residue was purified using column chromatography (SiO2, heptane-EtAOc 95:5) to give 0.82 g of 4-(2-bromo-ethyl)-2-fluoro-1-methoxy-benzene

後処理

  1. additionA mixture of resin
  2. temperaturecooled on an ice bath
  3. customThe cooling bath was removed
  4. filtrationwas filtered off
  5. washThe resin was washed with DCM
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was purified

出典と根拠

ORDレコード
ord-c0551eb6173e456eae4efd5ae274f767
出典データセット
uspto-grants-2013_01
特許番号
US08362049B2

反応ノート

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