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

HRID 2042968Notes

Reaction equation

HRID 2042968 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]=[CH:17][C:18]=1[C:2]#[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

Participants

3

Reactant 2

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

Product 1

HCID 25149895Ethyl 2-(4-(o-tolylethynyl)phenoxy)acetate

Procedure

The title compound was prepared from ethyl (4-ethynylphenoxy)acetate (42 mg, 0.21 mmol) and iodo-3-methylbenzene (0.03 mL, 0.20 mmol) according to the general procedure ID to give 43 mg (72%) of an orange oil after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:10). Rf: 0.22 (EtOAc:hexanes, 1:10); 1HNMR (CDCl3) δ 7.49-7.46 (m, 3H), 7.26-7.12 (m, 3H), 6.90-6.87 (m, 2H), 4.64 (s, 2H), 4.30-4.27 (dq, 2H, J=7.2 Hz, 2.1 Hz), 2.50 (s, 3H), 1.33-1.28 (tt, 3H, J=7.2 Hz, 1.5 Hz); 13CNMR (CDCl3) δ 168.6, 157.7, 140.0, 133.0, 131.7, 129.4, 128.1, 125.5, 123.2, 116.9, 114.7, 93.0, 87.4, 65.4, 61.5, 20.7, 14.1; EI-MS m/z 294 (M+).

Sources & evidence

ORD record
ord-1c4df2de1ce74d39baf97e502a97bed5
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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