Benzyl Bromide → HCID 22321881, compound

A solution of benzyl bromide (2.0 mL, 17.3 mmol) in THF (10 mL) was added dropwise at 0° C. to a stirred suspension of zinc dust (1.7 g, 26 mmol) in THF (10 mL) which had been activated according to the method described by Knochel (J.O.C. 53, 2392, 1988). The mixture was left to warm to ambient temperature and stir for 3 h. An aliquot (6.5 mmol) of the supernatent containing the benzyl zinc reagent was then added to a stirred solution of compound 27 (3.85 mmol) and Pd(dba)3 (0.0385 mmol) in THF (10 mL) at ambient temperature under argon. After 1 hr a second aliquot (6.5 mmol) of the benzyl zinc reagent was added. The resulting black reaction mixture was quenched with 2N HCl (250 mL) and extracted with Ethyl acetate (2×100 mL). The combined organics were washed with water (50 mL) and brine (50 mL), filtered through phase separating paper and evaporated to an orange gum. This was purified by chromatography on silica (Merck, 9385) eluting with 10% ethyl acetate/i-hexane to give methyl 2-benzyl-4-nitro-benzoic acid (compound 28).

1. waitThe mixture was left
2. customThe resulting black reaction mixture was quenched with 2N HCl (250 mL)
3. extractionextracted with Ethyl acetate (2×100 mL)
4. washThe combined organics were washed with water (50 mL) and brine (50 mL)
5. filtrationfiltered through phase
6. customseparating paper
7. customevaporated to an orange gum
8. customThis was purified by chromatography on silica (Merck, 9385)
9. washeluting with 10% ethyl acetate/i-hexane

ORD record

ord-2bb19d327dfe4fa6aa66ff12acbe89e9

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06946468B1