2-Amino-5-iodobenzonitrile → 2-Amino-5-(4'-fluorobenzyl)benzonitrile

HRID 853756Notes

Reaction equation

HRID 853756 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7](I)=[CH:6][C:3]=1[C:4]#[N:5].[Cl-].[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][Zn+])=[CH:15][CH:14]=1.NC1C=CC(CC2C=CC=CC=2)=CC=1C#N>>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:17][C:16]2[CH:19]=[CH:20][C:13]([F:12])=[CH:14][CH:15]=2)=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 3

HCID 99648032-Amino-5-iodobenzonitrileHCID 109436972-Amino-5-benzylbenzonitrileHCID 178505764HCID 178505764, compound

Product 1

HCID 117463182-Amino-5-(4'-fluorobenzyl)benzonitrile

Procedure

From 9 (488 mg, 2 mmol) and 4-fluorobenzylzinc chloride (0.5 M in THF, 10 mL, 5 mmol) by the same method as 10a; pale-yellow powder (275 mg, 51%): mp 105-107° C.; 1H NMR (CDCl3) δ 3.82 (s, 2H, CH2), 4.32 (br, 2H, NH2), 6.68 (d, J=8.8 Hz, 1H, H-3), 6.96-7.00 (m, 2H, 3′- and 5′-H), 7.08-7.14 (m, 3H, H-4, H-2′, and H-6′), 7.17 (s, 1H, H-6).

Sources & evidence

ORD record
ord-bf4847f494fd47b780bc526aa84937a4
Source dataset
uspto-grants-2007_08
Patent number
US07256197B2

Reaction notes

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