Sodium Carbonate → Methyl 4-(1-bromo-6-methoxynaphthalen-2-yl)benzoate

HRID 1771458Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[C:8]=1[Br:19])(=O)=O.[CH3:22][O:23][C:24]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)=[O:25].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO>[Br:19][C:8]1[C:9]2[C:14](=[CH:13][C:12]([O:17][CH3:18])=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[C:29]1[CH:30]=[CH:31][C:26]([C:24]([O:23][CH3:22])=[O:25])=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Followed the coupling procedure described for Example 1, starting from 1-bromo-6-methoxynaphthalen-2-yl trifluoromethanesulfonate (Intermediate 2) and 4-(methoxycarbonyl)phenylboronic acid with modifications: the base used was Na2CO3, the solvent was toluene/EtOH (4/1), and the reaction was heated to 80° C. for 3 h. The crude product was purified by silica gel column (PE/EtOAc=300/1 to 100/1), then washed with EtOAc (10 mL×5) to give the product (980 mg, yield 45%) as a white solid.

Workup

customThe crude product was purified by silica gel column (PE/EtOAc=300/1 to 100/1)
washwashed with EtOAc (10 mL×5)

Sources & evidence

ORD record: ord-71a20916c8864fc0a62a2e6a040aed4b
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249132B2

Reaction notes

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