1-Hydroxymethylbenzocyclobutene

Synthesis

Step A: Borane-THF solution (1M, 4 mL, 1.2 equiv) was slowly added dropwise to a solution of bicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid (500 mg, 3.38 mmol) in THF (6 mL) at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred overnight. Upon completion of the reaction, the reaction was quenched with water, the organic phase was extracted with EtOAc and dried with anhydrous MgSO4. Purification by silica gel column chromatography (eluent: 5-20% EtOAc/hexane gradient) afforded bicyclo[4.2.0]octa-1,3,5-trien-7-ylmethanol (388 mg, 86% yield).

References

[1] Patent: US2016/31875, 2016, A1. Location in patent: Paragraph 0276; 0277
[2] Journal of Medicinal Chemistry, 1965, vol. 8, p. 255 - 257