3-Iodotoluene → Ethyl 2-(4-(m-tolylethynyl)phenoxy)acetate

HRID 2042970Notes

Reaction equation

HRID 2042970 reaction equation
[C:1]([C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[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][CH:22]=[C:17]([C:2]#[C:1][C:3]2[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=2)[CH:18]=1

Participants

3

Reactant 2

HCID 122683-IodotolueneHCID 22450859Ethyl 2-(4-ethynylphenoxy)acetate

Product 1

HCID 25149896Ethyl 2-(4-(m-tolylethynyl)phenoxy)acetate

Procedure

The title compound was prepared from ethyl (4-ethynylphenoxy)acetate (42 mg, 0.21 mmol) and iodo-3-methylbenzene (0.04 mL, 0.31 mmol) according to the general procedure ID to give 56 mg (93%) of an orange oil after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:10). Rf: 0.44 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 7.61-7.56 (m, 2H), 7.51-7.31 (m, 4H), 7.03-6.88 (m, 2H), 4.75 (s, 2H), 4.43-4.36 (dq, 2H, J=7.2 Hz, 2.1 Hz), 2.47 (s, 3H), 1.44-1.38 (tt, 3H, J=7.2 Hz, 1.5 Hz); 13CNMR (CDCl3) δ 168.6, 157.7, 138.0, 133.1, 132.0, 128.9, 128.5, 128.2, 123.2, 116.2, 114.7, 88.6, 88.6, 65.4, 61.5, 21.2, 14.1; EI-MS m/z 294 (M+).

Sources & evidence

ORD record
ord-73e8b489e48549e08f1e2305aeaa4770
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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