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Year 1388: First Synagogue Approved
Rabbi Feinstein, in his book Ir Tehila (1886) dates the first documented permit to build a synagogue in Brisk to 1388:

from Ir Tehila, page 12
Courtesy of Hebrew Books.org
English translation:
According to ancient records found in the archive of Vilna, capital of Lita, Brisk was the first of all the Lithuanian communities that was granted a hurmana from Prince [Lithuanian Grand Duke] Witold (in the year 5148 – Common Era: 1388) to establish a community and build a synagogue...
Was the synagogue built immediately, or later? No document tells us. Rabbi Feinstein refers the reader to his sources:  Russki Yevrei periodical, Archives No. 1 and No. 40 and Voskhod [=East] 1881 No. 7.

The point at which the first synagogue was actually constructed was subject to confusion in Rabbi Feinstein's time. He also quotes in a footnote an 1883 article in the newspaper Hamelitz:

from Hamelitz, 5 March 1883

Translation:
In the old city the Jews had a glorious ancient building for a synagogue, built in 1385. It was built like a castle in which the Jews found shelter several times when they were in danger of harassment by their enemies. 
Rabbi Feinstein corrected the erroneous date in the newspaper HaTzfira later the same year:

from HaTzfira, 27 March 1883
The critical date is marked.
Translation:
On the basis of reliable records that we have in our hands, the community of Brisk obtained from Prince Witold the right to establish a community and to build a synagogue and a cemetery in 1388. It is obvious that prior to that there was no synagogue in Brisk.  
In his book History of the City of Brest-Litovsk (1016-1907), Zonnenberg, on page 25 echoes Rabbi Feinstein:
Witold was the first who [in a decree of 1388] allowed the Jews to establish community administration (self-government). He allowed the Brest Jews to build a synagogue and approved a plot for the Jewish cemetery. 
 
Notes:

Page Last Updated: 14-Sep-2016