1,2-Dichloroethane → 2-Bromomethyl-benzoic acid 2,2,2-trichloro-ethyl ester

HRID 709480

反応式

HRID 709480 の反応式
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[CH2:12](O)[C:13]([Cl:16])([Cl:15])[Cl:14].C(Cl)CCl.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl.O>[Cl:14][C:13]([Cl:16])([Cl:15])[CH2:12][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=1[CH2:2][Br:1]

参加物

8

反応物 4

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 8259TrichloroethanolHCID 3460032-(Bromomethyl)benzoic acid

生成物 1

HCID 668652492-Bromomethyl-benzoic acid 2,2,2-trichloro-ethyl ester収率 50%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a suspension of 2-(bromomethyl)benzoic acid (1.0 g, 4.65 mmol), β-trichloroethanol (0.54 mL, 5.58 mmol) and DMAP (0.057 g, 0.465 mmol) in DCM (20 mL) was added EDC×HCl (1.34 g, 6.98 mmol) at 0° C. The solution was stirred at 0° C. for 0.5 h and thereafter allowed to reach rt and stirred overnight. Water was added and the phases were separated through a phase separator. The organic portion was concentrated and the crude was submitted to flash chromatography using heptane and EtOAc (90/10) as eluent to yield the titled compound (0.80 g, 50%) as an oil; 1H NMR (400 MHz, CDCl3): δ 4.99 (s, 2H), 5.08 (s, 2H), 7.46 (m, 1H), 7.60 (m, 2H), 8.13 (d, 1H).

後処理

  1. customto reach rt
  2. stirringstirred overnight
  3. customthe phases were separated through a phase separator
  4. concentrationThe organic portion was concentrated

出典と根拠

ORDレコード
ord-d2c5b577b4ae454ea5bebed1adc951bc
出典データセット
uspto-grants-2015_11
特許番号
US09181181B2

関連ノート

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