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

HRID 1175322Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1175322
[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]

Komponenten

4

Edukt 2

HCID 1068Dimethyl SulfideHCID 59557689HCID 59557689, Verbindung

Produkt 1

HCID 595577063-(2-Bromo-5-chloro-4-(4-ethoxybenzyl)phenyl)propan-1-olAusbeute 55,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-96821a7a2dd5421c81212fa87301c251
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07838498B2

Notizen zur Reaktion

Wird geladen…