Reaktion #92147

Reaktionsgleichung

4-bromonaphthalene-1-carboxylic acid

BH3.THF

→

(4-bromonaphthalen-1-yl)methanol

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a 250-mL 3-necked round-bottom flask, was placed
2. 2
   workup.STIRRINGThe resulting solution was stirred overnight at room temperature
3. 3
   SonstigeThe reaction was then quenched by the addition of hydrogen chloride
4. 4
   workup.ADDITIONThe resulting solution was diluted with 200 mL of ethyl acetate
5. 5
   WaschenThe resulting mixture was washed with 3×100 mL of brine
6. 6
   TrocknenThe organic phase was dried over anhydrous sodium sulfate
7. 7
   Einengenconcentrated under vacuum
8. 8
   WaschenThe resulting residue was washed with 30 mL of n-hexane
9. 9
   SonstigeThis resulted in 6.3 g (95%) of (4-bromonaphthalen-1-yl)methanol as a white solid

Vorschrift

Into a 250-mL 3-necked round-bottom flask, was placed tetrahydrofuran (200 mL), 4-bromonaphthalene-1-carboxylic acid (7 g, 27.88 mmol, 1.00 equiv). This was followed by the addition of BH3.THF (55.7 mL, 2.00 equiv) dropwise with stirring. The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of hydrogen chloride. The pH was adjusted to 6. The resulting solution was diluted with 200 mL of ethyl acetate. The resulting mixture was washed with 3×100 mL of brine. The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The resulting residue was washed with 30 mL of n-hexane. This resulted in 6.3 g (95%) of (4-bromonaphthalen-1-yl)methanol as a white solid.

Quelle