Benzyl Bromide → 4-(Benzyloxy)-3-fluorobenzaldehyde

HRID 82779

Reaktionsgleichung

Reaktionsgleichung von HRID 82779
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C.O>[CH2:11]([O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[F:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

7

Edukt 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 5872503-Fluoro-4-hydroxybenzaldehyde

Produkt 1

HCID 219768984-(Benzyloxy)-3-fluorobenzaldehydeAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 3-fluoro-4-hydroxybenzaldehyde (4.264 g, 30.0 mmol), benzyl bromide (5.986 g, 35.0 mmol, 4.16 mL) and K2CO3 (820 g, 59.0 mmol) in DMF (50 mL) was stirred for 48 hours at room temperature before EtOAc (100 mL) and water (50 mL) were added. The organic layer was separated, washed with water (2×50 mL), brine (30 mL) and dried (Na2SO4). Concentration in vacuo gave a white solid residue. Recrystallization from CH2Cl2/n-hexane afforded CAB06038 as colorless needles (5.59 g, 81%). Mp. 94-95° C.; 1H NMR (400 MHz, CDCl3) δ 524 (s, 2H), 7.12 (dd, J=8.2, 8.2 Hz, 1H), 734-7.48 (m, 5H), 7.59-7.66 (m, 2H), 9.85 (d, J=2.0 Hz, 1H); LRMS (ES+): m/z 231.1 (100%, [M+H]+).

Aufarbeitung

  1. additionwere added
  2. customThe organic layer was separated
  3. washwashed with water (2×50 mL), brine (30 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationConcentration in vacuo
  6. customgave a white solid residue
  7. customRecrystallization from CH2Cl2/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-3841b984b0134e28bf554ba3eafab8b1
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846737B2

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