Roof fall is a frequent and destructive disaster in the working face of extra-thick coal seams. The important technology for disaster elimination is roof grouting, and the key to its success is to accurately predict the distance of the advanced fractures based on a reasonable rock constitutive relationship. In this paper, the constitutive relationship reflecting the progressive failure process of rock was established, including the elastic–plastic constitutive relation of intact rock, the fracture constitutive relation of non-penetrating fracture, and the shear friction constitutive relation of penetrating fracture. On this basis, the finite–discrete element method (FDEM) numerical calculation method was developed. Taking Yushupo Coal mine with a 16-m-thick coal seam as an example, the numerical results showed that the fractures in the roof appear 15~35 m ahead of the working face, and the maximum value of advance bearing pressure is between 16 and 30 MPa. Meanwhile the laboratory test results showed that the compressive strength of the grouted coal is 14.91 MPa after solidification for 7d. The above data mean that the grouting slurry can solidify the broken roof into a whole without roof fall disaster. At the same time, the rock pressure of the extra-thick coal seam can effectively crush the top coal, which is conducive to the top-coal caving operation. The in situ test shows that when the pre-grouting is carried out in the range of 20~30 m in front of the working face, the roof fall disaster can be effectively avoided, which is consistent with the numerical simulation results. It shows the rationality of the FDEM numerical method and the constitutive model of rock deformation–fragmentation failure process.