Phenylacetyl chloride → HCID 64793016, compound

Sodium bicarbonate (1.0 g, 12.2 mmol) was added portion-wise to a stirred solution of (4-amino-phenyl)-methanol (0.5 g, 4.06 mmol) in a 1:1 mixture of THF:H2O (16 ml) and the mixture was stirred at room temperature for 5 minutes. After this time, benzyl carbonyl chloride (0.69 g, 4.06 mmol) was added dropwise, followed by a further portion of sodium bicarbonate (0.5 g, 6.1 mmol) and stirring was continued for 1 hour. The reaction mixture was then diluted with DCM (50 ml) and washed sequentially with HCl (1M solution, 10 ml) then NaOH (1M solution, 10 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated. The resulting residue was purified by flash column chromatography (elution: 50% EtOAc, 50% heptane) to give the title compound (0.6 g, 57% yield) as an off-white solid. δH (500 MHz, DMSO) 9.63 (s, 1 H) 7.01-7.39 (m, 9 H) 4.90-5.11 (m, 3 H) 4.30 (d, J=5.63 Hz, 2 H).

1. washwashed sequentially with HCl (1M solution, 10 ml)
2. customThe organic layer was separated
3. dry with materialdried (MgSO4)
4. filtrationfiltered
5. concentrationconcentrated
6. customThe resulting residue was purified by flash column chromatography (elution: 50% EtOAc, 50% heptane)

ORD record

ord-16ec991b84fa40cdade2f542728c1d72

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08889716B2