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

HRID 1175322Notes

Reaction equation

HRID 1175322 reaction equation
[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]

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 59557689HCID 59557689, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-96821a7a2dd5421c81212fa87301c251
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

Loading…