1,4-Dibromobutane → 1-[4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]cyclopentanecarbonitrile

HRID 7719

Reaction equation

HRID 7719 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]([CH2:16][C:17]#[N:18])=[C:12]([Cl:19])[CH:11]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:31][CH2:32][CH2:33][CH2:34]Br>C1COCC1>[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:17]#[N:18])[CH2:34][CH2:33][CH2:32][CH2:31]2)=[C:12]([Cl:19])[CH:11]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 10286072[4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]acetonitrile

Product 1

HCID 102865191-[4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]cyclopentanecarbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]acetonitrile (270 mg, 1.0 mmol) and THF (20 mL) was cooled to −78° C. A solution of NaHMDS (3.7 mL, 2.2 mmol, 0.6M solution in PhMe) was added dropwise via syringe to the reaction. After 15 min at −78° C., 1,4-dibromobutane (143 μL, 1.2 mmol) was added dropwise via syringe. The cooling bath was removed, and the reaction was allowed to warm to rt. The reaction was quenched by the addition of silica gel (600 mg) and concentrated to dryness. The residue was purified by flash chromatography on silica gel (EtOAc:hexanes 1:5) to afford the desired 1-[4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]cyclopentanecarbonitrile as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.34 (s, 1H), 8.12 (dd, 1H), 7.77–7.80 (m, 1H), 7.56–7.62 (m, 2H), 7.35–7.42 (m, 2H), 2.71–2.78 (m, 2H), 2.14–2.26 (m, 2H), 1.89–2.01 (m, 4H). MS (ESI) 323 (M+H)+.

Workup

  1. customThe cooling bath was removed
  2. customThe reaction was quenched by the addition of silica gel (600 mg)
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by flash chromatography on silica gel (EtOAc:hexanes 1:5)

Sources & evidence

ORD record
ord-f11ad2c55b7f49aca6d002758dd0a103
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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