Pyridine → Phenol, 4-[(2-chloroethyl)thio]-

To a solution of 5.0 g 4-(2-hydroxy-ethylsulfanyl)-phenol (29 mmol) in 100 ml CH2,Cl2 were added at 0° C. 2.6 ml pyridine (32.3 mmol) and 2.34 ml SOCl2 (32.3 mmol), dissolved in 10 ml CH2Cl2. The reaction mixture was stirred for 1 h at r.t. and then quenched by the addition of water. The organic phase was separated and washed twice with sat. NaHCO3-solution. The combined aqueous phases were extracted with CH2Cl2 twice and the combined organic layers were dried over MgSO4 and the solvent was removed under reduced pressure to give 4.6 g product (24.3 mmol, 83%) as a yellow oil.

1. customquenched by the addition of water
2. customThe organic phase was separated
3. washwashed twice with sat. NaHCO3-solution
4. extractionThe combined aqueous phases were extracted with CH2Cl2 twice
5. dry with materialthe combined organic layers were dried over MgSO4
6. customthe solvent was removed under reduced pressure

ORD record

ord-32d266a0c12341ecb5cc69d359f37281

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06310213B1