4-Bromo-1-naphthoic acid → (4-Bromonaphthalen-1-yl)methanol

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.

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

ORD record

ord-dba447df011e47768477ed7196060fe7

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09447084B2