4-Chloro-2-hydroxybenzonitrile → 4-Chloro-2-[[(1R)-3-chloro-1-(2-thienyl)propyl]oxy]benzonitrile

HRID 2179966Notes

Reaction equation

HRID 2179966 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([OH:10])[CH:3]=1.[Cl:11][CH2:12][CH2:13][C@@H:14]([C:16]1[S:17][CH:18]=[CH:19][CH:20]=1)O>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C@@H:14]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)[CH2:13][CH2:12][Cl:11])[CH:3]=1

Participants

3

Reactant 2

HCID 34427894-Chloro-2-hydroxybenzonitrileHCID 10236042(S)-3-Chloro-1-(thiophen-2-yl)propan-1-ol

Product 1

HCID 698025914-Chloro-2-[[(1R)-3-chloro-1-(2-thienyl)propyl]oxy]benzonitrile

Procedure

Using 4-chloro-2-hydroxybenzonitrile (303 mg, 1.97 mmol) and (S)-α-(2-chloroethyl) thiophenemethanol (349 mg, 1.97 mmol), and the procedure described in Example 5(a), the title compound was prepared as a white crystalline solid (373 mg, 61%).

Sources & evidence

ORD record
ord-602e5c1fe0f8430c8b73d02b19cfdb57
Source dataset
uspto-grants-2005_05
Patent number
US06887871B2

Reaction notes

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