Hydrochloric Acid → 4-(Anilinocarbonyl)-3-methoxyphenylboronic acid

HRID 432258Notes

Reaction equation

HRID 432258 reaction equation
C([Li])CCC.[C:6]1([NH:12][C:13](=[O:23])[C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][C:15]=2[O:21][CH3:22])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[B:24](OC(C)C)([O:29]C(C)C)[O:25]C(C)C.Cl>O1CCCC1>[NH:12]([C:13]([C:14]1[CH:19]=[CH:18][C:17]([B:24]([OH:29])[OH:25])=[CH:16][C:15]=1[O:21][CH3:22])=[O:23])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 223472094-Bromo-2-methoxy-N-phenylbenzamideHCID 178418339Butyllithium

Product 1

HCID 223469054-(Anilinocarbonyl)-3-methoxyphenylboronic acidYield 62.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyl lithium (1.6 M in hexane solution, 5.1 ml, 8.16 mmol) was added slowly to a solution of N1-phenyl-4-bromo-2-methoxybenzamide (1.0 g, 3.26 mmol) in tetrahydrofuran (25 mL) at −78° C. After 30 minutes, triisopropyl borate (1.13 mL, 4.90 mmol) was added rapidly. The reaction mixture was allowed to warm up to room temperature after 15 minutes and stirred at room temperature for 16 hours. Hydrochloric acid (2.5N, 18 mL) was added and the mixture was stirred for 5 h hours. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The residue was re-crystallized from ethyl acetate/heptane to give 4-(anilinocarbonyl)-3-methoxyphenylboronic acid (0.549 g, 62%). 1H NMR (DMSO-d6) δ 3.91 (s, 3H), 7.08 (m, 1H), 7.33 (m, 2H), 7.47 (d, J=7.57 Hz, 1H), 7.59 (m, 2H), 7.73 (d, J=7.36 Hz, 2H), 8.24 (s, 2H), 10.10 (s, 1H).

Workup

  1. stirringthe mixture was stirred for 5 h hours
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was re-crystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-ec2eb1ab81d04fc18f4302f23f378afa
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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