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In study of the brain, oxygenation changes in the cerebral cortex are of great interest, since the concentrations of oxyhaemoglobin and deoxyhaemoglobin change due to coupling of hemodynamics to cortical neural activity. In order to non-invasively monitor oxygenation in the cerebral cortex by near-infrared spectroscopy (NIRS), light should penetrate into brain tissue to a depth of approximately 1-2 cm. Many studies show that by increasing the source-detector distance, illuminating light penetrates deeper into brain tissue. Using tissue-mimicking phantom measurements, forehead in vivo measurements, and Monte Carlo (MC) simulations, this paper estimates light propagation in the brain and the minimum source-detector distance to allow sensing of the cerebral cortex. We present optical sensing of a pulsating aqueous intralipid suspension in a vessel located at different depths within a multilayered phantom of the human forehead. Experimental results are compared with the MC simulations accounting for the optical properties of the phantom. The thickness and morphology of the different tissue layers were obtained from an anatomical magnetic resonance image of a test subject's head. Results from these three methods correlate with each other and show that the brain cortex can be sensed with optical methods based on NIRS.