Thionyl bromide → 1-(Bromomethyl)-4-(2-chloroethoxy)benzene

HRID 722073ノート

反応式

HRID 722073 の反応式
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9]O)=[CH:7][CH:6]=1.S(Br)([Br:15])=O>O1CCOCC1.CCOCC>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][Br:15])=[CH:7][CH:6]=1

参加物

5

反応物 2

HCID 68176Thionyl bromideHCID 21882321[4-(2-Chloroethoxy)phenyl]methanol

生成物 1

HCID 218822521-(Bromomethyl)-4-(2-chloroethoxy)benzene収率 58%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 312751,4-Dioxane溶媒

実験手順

To 4-(2-Chloroethoxy)benzylalcohol CAS No. [111728-87-1] (6.4 g, 34.31 mmol) in dioxane (100 mL) at 0° C. was added slowly thionylbromide (7.13 g, 34.31 mmol). The reaction was run at 0° C. after 5 min. The reaction mixture was diluted with ether (200 mL) and washed with H2O (1×30 mL) then NaHCO3 (2×25 mL), and brine (30 mL). The organic extract was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography (15% EtOAc/Hex) to yield 5.0 g (58%) of the desired product. Mp=64–66° C.; 1H NMR (DMSO) 7.37 (d, 2 H, J=8.8 Hz), 6.93 (d, 2 H, J=8.8 Hz), 4.68 (s, 2 H), 4.24 (t, 2 H, J=5.05 Hz), 3.93 (t, 2 H, J=5.27 Hz); MS eI m/z 248 (M+).

後処理

  1. washwashed with H2O (1×30 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel chromatography (15% EtOAc/Hex)

出典と根拠

ORDレコード
ord-5a308b0d94bc44efb797fbd16a4cc9f9
出典データセット
uspto-grants-2006_11
特許番号
US07138392B2

反応ノート

読み込み中…