Myristyl bromide → HCID 12361490, compound

HRID 874704Notes

Reaction equation

HRID 874704 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12]([OH:14])[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[C:12]([O:14][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])[CH:13]=[C:4]([C:3]([O:2][CH3:1])=[O:15])[CH:5]=1

Participants

5

Reactant 3

HCID 8208Myristyl bromideHCID 11430Potassium CarbonateHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

Product 1

HCID 12361490HCID 12361490, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product was generated using general protocol D using dimethyl-5-hydroxyisophthalate (1.037 g, 4.93 mmol), 1-bromotetradecane (1.34 mL, 4.48 mmol), K2CO3 (2.48 g, XXmol), CH3CN (50 mL) yielded 1.21 g (60.2%) of a white solid. 1H NMR (CDCl3, 400 MHz) δ: 8.2607 (s, 1H, Ar—H), 7.7396 (s, 2H, Ar—H), 4.0315 (t, 2H, O—CH2, 3J=6.62 Hz), 3.9374 (s, 6H, COOCH3), 1.8046 (p, 2H, O—CH2—CH23J=6.82 Hz), 1.4660 (p, 2H, O—CH2—CH2—CH2, 3J=6.86 Hz), 1.2582 (m, 22H), 0.8809 (t, 3H, CH2—CH3, 3J=6.69 Hz

Sources & evidence

ORD record
ord-02d71d86c9a243c2accf745997cef90e
Source dataset
uspto-grants-2015_03
Patent number
US08980925B2

Reaction notes

Loading…