3-Bromobenzaldehyde → HCID 86654700, compound

HRID 2042981Notes

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:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=[O:20]>>[CH:19]([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:23]=[CH:22][CH:21]=1)=[O:20]

Participants

Reactant 2

HCID 765833-Bromobenzaldehyde

HCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 86654700HCID 86654700, compound

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (102 mg, 0.54 mmol) and 3-bromobenzaldehyde (0.09 mL, 0.62 mmol) according to the general procedure IC to give 93 mg (59%) of an orange solid after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:3). Rf: 0.16 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 10.01 (s, 1H), 8.02 (s, 1H), 7.84-7.74 (m, 2H), 7.54-7.46 (m, 3H), 7.26-7.19 (m, 2H), 3.67 (s, 3H), 3.00-2.95 (t, 2H, J=7.8 Hz), 2.67-2.62 (t, 2H, J=7.8 Hz); 13CNMR (CDCl3) δ 191.6, 173.0, 141.4, 137.0, 136.5, 132.9, 131.8, 129.1, 128.8, 128.4, 124.6, 120.6, 90.9, 87.6, 51.6, 35.3, 30.8; EI-MS m/z 292 (M+).

Sources & evidence

ORD record: ord-58f807ef0a784f6c84a14f7a82488811
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586607B2

Reaction notes

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