2-(2-Bromophenyl)ethan-1-ol → Methyl 3-(4-((2-(2-hydroxyethyl)phenyl)ethynyl)phenyl)propanoate

HRID 2043025Notes

Reaction equation

HRID 2043025 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:24]=[CH:23][CH:22]=[CH:21][C:17]=1[CH2:18][CH2:19][OH:20]>>[OH:20][CH2:19][CH2:18][C:17]1[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=1[C:2]#[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

Participants

3

Reactant 2

HCID 27340892-(2-Bromophenyl)ethan-1-olHCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Product 1

HCID 58319091Methyl 3-(4-((2-(2-hydroxyethyl)phenyl)ethynyl)phenyl)propanoate

Procedure

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (107 mg, 0.57 mmol) and 2-bromophenethyl alcohol (100 μL, 0.74 mmol) according to the general procedure IF to give 83 mg (47%) of a dark orange oil after purification by flash chromatography (SiO2, EtOAc:PE, 1:1). Rf=0.19 (EtOAc:PE, 1:1); 1HNMR (CDCl3): δ 7.46-7.44 (m, 1H), 7.38-7.36 (m, 2H), 7.21-7.20 (m, 2H), 7.18-7.14 (m, 1H), 7.13-7.10 (m, 2H), 3.91-3.87 (m, 2H), 3.60 (s, 3H), 3.06 (t, J=5.1 Hz, 2H), 2.89 (t, J=5.7 Hz, 2H), 2.56 (t, J=5.4 Hz, 2H); 13CNMR (CDCl3): δ 173.1, 141.1, 140.4, 132.4, 131.7, 131.7, 129.7, 128.5, 126.6, 123.2, 121.2, 93.2, 87.6, 62.9, 51.7, 38.1, 35.4, 30.9.

Sources & evidence

ORD record
ord-2a46e0686a6c4a48960a65eddf4b2cd4
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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