3'-Bromoacetophenone → HCID 65145097, compound

HRID 2098514Notes

Reaction equation

[CH2:1]([Mg]Cl)[CH2:2][CH2:3][CH3:4].[Br:7][C:8]1[CH:9]=[C:10]([C:14](=[O:16])[CH3:15])[CH:11]=[CH:12][CH:13]=1>>[Br:7][C:8]1[CH:9]=[C:10]([C:14]([OH:16])([CH2:1][CH2:2][CH2:3][CH3:4])[CH3:15])[CH:11]=[CH:12][CH:13]=1

Participants

Reactant 2

HCID 165023'-Bromoacetophenone

HCID 178418265HCID 178418265, compound

Product 1

HCID 65145097HCID 65145097, compound

Procedure

Grignard coupling of butylmagnesium chloride with 1-(3-bromophenyl)ethanone followed by flash chromatography (0-25% ethyl acetate/hexanes gradient), gave 2-(3-bromophenyl)hexan-2-ol as a yellow oil. Yield (0.99 g, 51%): 1H NMR (400 MHz, CDCl3) δ 7.59 (t, J=2.0 Hz, 1H), 7.30-7.37 (m, 2H), 7.19 (t, J=8.0 Hz, 1H), 1.70-1.84 (m, 2H), 1.52 (s, 3H), 1.64 (brs, 1H), 1.18-1.30 (m, 3H), 1.02-1.14 (m, 1H), 0.84 (t, J=7.2 Hz, 3H).

Sources & evidence

ORD record: ord-dd042f746c8045fdaed0b8361acabf1d
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450527B2

Reaction notes

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