1,5-Dibromopentane → 1-[4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]cyclohexanecarbonitrile

HRID 7720

Reaction equation

HRID 7720 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:21]#[N:22])[CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:12]([Cl:23])[CH:11]=1.O1C2C=CC=CC=2N=[C:25]1C1C=CC(CC#N)=C(Cl)C=1.BrCCCCCBr>>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:21]#[N:22])[CH2:25][CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:12]([Cl:23])[CH:11]=1

Participants

4

Reactant 3

HCID 81001,5-DibromopentaneHCID 10286072[4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]acetonitrileHCID 102865191-[4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]cyclopentanecarbonitrile

Product 1

HCID 101721151-[4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]cyclohexanecarbonitrile

Procedure

Utilizing the general procedure outlined for 1-[4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]cyclopentanecarbonitrile, [4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]acetonitrile (400 mg, 1.5 mmol) and 1,5-dibromopentane (250 μL, 1.8 mmol) reacted to afford the desired 1-[4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]cyclohexanecarbonitrile as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.22 (d, 1H), 8.06 (d, 1H), 7.68–7.73 (m, 1H), 7.51–7.55 (m, 2H), 7.28–7.35 (m, 2H), 2.49 (d, 2H), 1.73–2.00 (m, 8H). MS (ESI) 337 (M+H)+.

Workup

  1. customreacted

Sources & evidence

ORD record
ord-2d4b0f70fe88423db019e11bd28d183d
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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