1-Bromo-3-(isocyanomethyl)benzene → HCID 86654701, compound

HRID 2043012Notes

Reaction equation

HRID 2043012 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)#[CH:2].Br[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N+:23]#[C-:24])[CH:17]=1>>[N+:23]([CH2:22][C:18]1[CH:17]=[C:16]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=2)[CH:21]=[CH:20][CH:19]=1)#[C-:24]

Participants

3

Reactant 2

HCID 38872091-Bromo-3-(isocyanomethyl)benzeneHCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 86654701HCID 86654701, compound

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (95 mg, 0.50 mmol) and 1-bromo-3-(isocyanomethyl)benzene (117 mg, 0.60 mmol) according to the general procedure IC to give 109 mg (71%) of a pale yellow oily product after purification by flash chromatography (SiO2, EtOAc:PE, 1:5). Rf=0.27 (EtOAc:PE, 1:2); 1H NMR (CDCl3) δ 7.51-7.44 (m, 4H), 7.36 (t, J=7.7 Hz, 1H), 7.31-7.27 (m, 1H), 7.19 (d, J=8.3 Hz, 2H), 3.73 (s, 2H), 3.67 (s, 3H), 2.97 (t, J=7.7 Hz, 2H), 2.64 (t, J=7.7 Hz, 2H); 13C NMR (CDCl3) δ 173.1, 141.2, 131.8, 131.2, 131.0, 130.2, 129.2, 128.4, 127.6, 124.5, 120.8, 117.5, 90.3, 88.1, 51.7, 35.4, 30.8, 23.4; ESI-MS m/z 326.1 (M+Na+).

Sources & evidence

ORD record
ord-e630e2dde2eb4194adf995fd17187b57
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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