4-Bromo-3-fluorobenzaldehyde → 1-(4-Bromo-3-fluorophenyl)ethan-1-ol

HRID 1501208

반응식

HRID 1501208 반응식
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[F:10].[CH3:11][Mg]Br>O1CCCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH3:11])=[CH:4][C:3]=1[F:10]

참가 물질

4

반응물 2

HCID 27834114-Bromo-3-fluorobenzaldehydeHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 717565421-(4-Bromo-3-fluorophenyl)ethan-1-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-bromo-3-fluorobenzaldehyde (5 g, 24.75 mmol) in anhydrous tetrahydrofuran (100 mL) was added methyl magnesium bromide (3 M solution in tetrahydrofuran, 8.21 mL) at −45° C. under the atmosphere of nitrogen then stirred at room temperature. After 2 hours, LC-MS showed the desired product has received. The aqueous of ammonium chloride (15 mL) was added to quench the reaction, and extracted with ethyl acetate (50 mL), combined and concentrated the organic layers. The crude product was purified by column chromatography (petroleum ether/ethyl acetate=1:1) to give 1-(4-bromo-3-fluorophenyl)ethanol (4 g, 78%). LCMS (M+H+) m/z: calcd 217.97. found 218. 1H NMR (300 MHz, CD3OD): δ 7.92-7.87 (m, 1H), 7.23-7.19 (m, 1H), 7.07-7.10 (m, 1H), 4.80 (d, J=6.3 Hz, 1H), 1.41 (t, J=2.7 Hz, 3H).

출처 및 근거

ORD 기록
ord-86254549ae6742c5aa12c4c86923c28f
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206128B2

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