Dimethyl Sulfide → 3-(2-Bromo-5-chloro-4-(4-ethoxybenzyl)phenyl)propan-1-ol

HRID 1175322ノート

反応式

HRID 1175322 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)[C:5]([Cl:18])=[CH:4][C:3]=1[CH2:19][CH2:20][C:21](O)=[O:22].S(C)C>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH3:17])=[CH:13][CH:14]=2)[C:5]([Cl:18])=[CH:4][C:3]=1[CH2:19][CH2:20][CH2:21][OH:22]

参加物

4

反応物 2

HCID 1068Dimethyl SulfideHCID 59557689HCID 59557689、化合物

生成物 1

HCID 595577063-(2-Bromo-5-chloro-4-(4-ethoxybenzyl)phenyl)propan-1-ol収率 55.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred 0° C. solution of 3-(2-bromo-5-chloro-4-(4-ethoxybenzyl)phenyl) propanoic acid (BK) (0.5 g, 1.26 mmol) in 8 mL of THF was added BH3 in Me2S (2M, 3.15 mL, 6.29 mmol). After stirring for 30 min at 0° C., the mixture was warmed to room temperature and stirred overnight. The reaction solution was slowly quenched with dropwise addition of water until no more gas evolved. The reaction mixture was taken up in 20 mL of ethyl acetate, washed with saturated Na2CO3, water and brine, and then dried over Na2SO4, filtered and concentrated to obtain 0.268 g of crude intermediate BL, which was used in the next step without further purification.

後処理

  1. temperaturethe mixture was warmed to room temperature
  2. stirringstirred overnight
  3. customThe reaction solution was slowly quenched with dropwise addition of water until no more gas
  4. washwashed with saturated Na2CO3, water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-96821a7a2dd5421c81212fa87301c251
出典データセット
uspto-grants-2010_11
特許番号
US07838498B2

反応ノート

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