Yield:848170-46-7 65%

Reaction Conditions:

Stage #1: m-Bromoanilinewith sodium hydride in tetrahydrofuran;mineral oil; for 6 h;Inert atmosphere;
Stage #2: 5-Chlorovaleroyl chloride in tetrahydrofuran;mineral oil at 20; for 6 h;Inert atmosphere;

Steps:

5-Chloro-N-(3-hydroxyphenyl)pentanamide 10f

General procedure: To a stirred solution of 3-aminophenol (1.50 g, 14.0 mmol) in THF (30 mL) under nitrogen was added NaH (60 % dispersion in mineral oil; 0.60 g, 24 mmol) in small portions to permit controlled evolution of hydrogen. 5-Chloropropionyl chloride (1.31 mL, 14.0 mmol) was then added through a septum and the resulting solution was stirred for ca. 6 h. The solvent was evaporated in vacuo and the residue dissolved in EtOAc (2 x 50 mL). The organic solution was washed sequentially with satd. aq. NaHCO₃ (2 × 100 mL), water(2 x 100 mL) and brine (2 × 100 mL). The aqueous washings were extracted with EtOAc and the combined organic solutions were dried (anhydr. MgSO₄). Evaporation of the solvent in vacuo afforded 5-chloro-N-(3-hydroxyphenyl)pentanamide 10f as a brown gum (2.42 g, 76 %)

References:

Bodill, Taryn;Conibear, Anne C.;Mutorwa, Marius K.M.;Goble, Jessica L.;Blatch, Gregory L.;Lobb, Kevin A.;Klein, Rosalyn;Kaye, Perry T. [Bioorganic and Medicinal Chemistry,2013,vol. 21,# 14,p. 4332 - 4341] Location in patent:supporting information