3-Bromobiphenyl → 3-(3-(Biphenyl-3-ylethynyl)phenyl)propan-1-ol

HRID 2098487Notes

Reaction equation

HRID 2098487 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:7][CH:8]=1)#[CH:2].Br[C:14]1[CH:15]=[C:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=[CH:18][CH:19]=1>>[C:16]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:17]=[CH:18][CH:19]=[C:14]([C:2]#[C:1][C:3]2[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:7][CH:8]=2)[CH:15]=1

Participants

3

Reactant 2

HCID 164493-BromobiphenylHCID 576083943-(3-Ethynylphenyl)propan-1-ol

Product 1

HCID 576085113-(3-(Biphenyl-3-ylethynyl)phenyl)propan-1-ol

Procedure

Coupling of alcohol 50 with 3-bromobiphenyl was conducted following the method described in Example 21 to give 3-(3-(biphenyl-3-ylethynyl)phenyl)propan-1-ol. Purification by flash chromatography (5% EtOAc-hexanes) gave a brown oil. Yield (0.560 g, 67%): 1H NMR (400 MHz, CDCl3) δ 7.78 (br s, 1H), 7.61 (d, J=7.2 Hz, 2H), 7.56 (d, J=7.6 Hz, 1H), 7.51 (d, J=8.0 Hz, 1H), 7.37-7.48 (m, 6H), 7.29 (d, J=7.6 Hz, 1H), 7.19 (d, J=7.6 Hz, 1H), 3.70 (dt, J=6.2, 5.2 Hz, 2H), 2.73 (t, J=7.6 Hz, 2H), 1.92 (quint, J=6.8 Hz, 2H), 1.27 (t, J=5.2 Hz, 1H).

Sources & evidence

ORD record
ord-2150541351264e66822d328b962d6c7d
Source dataset
uspto-grants-2013_05
Patent number
US08450527B2

Reaction notes

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