Boron tribromide → HCID 86583670, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-methoxy-4-[5′-(8-phenyl-octylcarbamoyl)-3,3″-bis-trifluoromethyl-[1,1′;3′,1″]terphenyl-2′yloxymethyl]-benzoic acid methyl ester (0.418 g, 0.53 mmol, 1 eq) in CH2Cl2 (9 mL) cooled to 0° C. was added BBr3 (1M in CH2Cl2) (0.800 mL, 0.53 mmol, 1 eq). The reaction was stirred at 0° C. for 40 min, poured over ice and extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (20 to 30% EtOAc:hexane+1% Formic Acid) to afford 2-hydroxy-4-[5′-(8-phenyl-octylcarbamoyl)-3,3″-bis-trifluoromethyl-[1,1′;3′,1″]terphenyl-2′yloxymethyl]-benzoic acid methyl ester (see next example) and the title compound (0.201 g, 50%) as a white foam. 1H NMR (DMSO-d6) δ 13.60 (bs, 1H); 11.10 (bs, 1H); 8.59 (bt, 1H); 7.96-7.92 (m, 6H); 7.78-7.66 (m, 4H); 7.48 (d, 1H); 7.26-7.10 (m, 5H); 6.26. (d, 1H); 6.21 (dd, 1H); 4.18 (dd, 2H); 3.24 (dd, 2H); 2.52 (t, 2H); 1.52 (m, 4H); 1.27 (m, 8H); IR (film) 3300, 2950, 2800, 1680, 1630, 1590, 1540, 1440, 1320, 1260, 1205, 1160, 1120, 1095, 1080, 990 cm−1; mass spectrum [(−)ESI], m/z 776 (M−H)−; Anal. Calcd. for C43H39F6NO5: C, 67.62; H, 5.15; N, 1.83, Found: C, 67.21; H, 5.11; N, 1.71.

Provenance & Evidence