3-Iodotoluene → HCID 58319115, compound

HRID 2043009Notes

Reaction equation

HRID 2043009 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:11][CH:10]2[C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=1)#[CH:2].I[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=1>>[C:19]1([CH3:23])[CH:20]=[CH:21][C:22]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][C:6]([CH:9]3[CH2:11][CH:10]3[C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=2)=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 122683-IodotolueneHCID 58319131Methyl 2-(4-ethynylphenyl)cyclopropanecarboxylate

Product 1

HCID 58319115HCID 58319115, compound

Procedure

The title compound was prepared from methyl 2-(4-ethynylphenyl)cyclopropanecarboxylate (80 mg, 0.40 mmol) and 1-iodo-3-methylbenzene (97 mg, 0.44 mmol) according to the general procedure IF to give 57 mg (49%) of a white after purification by flash chromatography (SiO2, EtOAc:PE, 1:9): Rf=0.43 (EtOAc:PE, 1:4); 1H NMR (CDCl3) δ 7.46-7.38 (m, 4H), 7.14 (d, J=7.9 Hz, 2H), 7.06 (d, J=8.2 Hz, 2H), 3.72 (s, 3H), 2.59-2.47 (m, 1H), 2.36 (s, 3H), 1.92 (ddd, J=8.5, 5.3, 4.2 Hz, 1H), 1.63 (dt, J=9.9, 5.0 Hz, 1H), 1.33 (ddd, J=8.4, 6.5, 4.7 Hz, 1H); 13C NMR (CDCl3) δ 173.6, 140.2, 138.4, 131.6, 131.5, 129.1, 126.1, 121.6, 120.2, 89.6, 88.5, 52.0, 26.2, 24.2, 21.5, 17.2; ESI-MS m/z 313.1 (M+Na+).

Workup

  1. customto give 57 mg (49%) of a
  2. customwhite after purification by flash chromatography (SiO2, EtOAc:PE, 1:9)

Sources & evidence

ORD record
ord-1f904cbc8c8d4f32a3ab6bca059bb75b
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

Loading…