Reaction #1005997

ord-14d41158444f487fbc684ad3b4f69e63

Reaction equation

COC(=O)c1cccc(Br)c1
methyl 3-bromobenzoate
CC(C)(C)c1ccc(N)cc1
4-tert-butylaniline
→
COC(=O)c1cccc(Nc2ccc(C(C)(C)C)cc2)c1
3-[N-(4-tert-Butylphenyl)amino]benzoic acid methyl ester

Reactants

COC(=O)c1cccc(Br)c1
methyl 3-bromobenzoate
CC(C)(C)c1ccc(N)cc1
4-tert-butylaniline
—
methyl ester
—
Compound 10

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Reaction of methyl 3-bromobenzoate with 4-tert-butylaniline according to general procedure A provided methyl ester of Compound 10 as a yellow oil (81% yield). 1H NMR (CDCl3, 500 MHz): δ=7.73 (s, 1H), 7.57 (d, J=7.6 Hz, 1H), 7.21-7.42 (m, 4H), 7.06-7.13 (m, 2H), 5.85 (s, 1H), 3.92 (s, 3H), 1.36 (s, 9H). 13C NMR (CDCl3, 125 MHz): δ=167.4, 145.1, 144.3, 139.8, 131.4, 129.4, 126.4, 121.3, 120.9, 118.9, 117.7, 52.3, 34.4, 31.6.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09271961B2uspto-grants-2016_03