Methyl 4-Bromo-2-chlorobenzoate → Methyl 2-chloro-4-vinylbenzoate

HRID 514542Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([Cl:12])[CH:3]=1.[K+].[CH:14]([B-](F)(F)F)=[CH2:15]>>[Cl:12][C:4]1[CH:3]=[C:2]([CH:14]=[CH2:15])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

Reactant 2

HCID 22058730Methyl 4-Bromo-2-chlorobenzoate

HCID 23679353Potassium vinyltrifluoroborate

Product 1

HCID 57461224Methyl 2-chloro-4-vinylbenzoate

Procedure

The title compound was prepared from methyl 4-bromo-2-chlorobenzoate and vinyltrifluoroborate potassium salt according to the procedure for the preparation of Example 135, part A. 1H NMR (400 MHz, CDCl3): δ 3.92 (3H, s), 5.41 (1H, d, J=11.2 Hz), 5.85 (1H, d, J=9.2 Hz), 6.66 (1H, dd, J=11.2 Hz, 17.6 Hz), 7.32 (1H, d, J=8.0 Hz), 7.47 (1H, s), 7.81 (1H, d, J=8.0 Hz).

Sources & evidence

ORD record: ord-e37cbcd76e83416ab2b8999c1ed69448
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09107916B2

Reaction notes

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