Bromine → HCID 86698556, compound

HRID 1749006Notes

Reaction equation

HRID 1749006 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:13])[CH2:11][CH3:12])[CH:5]=[CH:6][C:7]=1[F:8].[Br:14]Br>C(O)(=O)C>[Br:14][C:5]1[CH:6]=[C:7]([F:8])[C:2]([Cl:1])=[CH:3][C:4]=1[NH:9][C:10](=[O:13])[CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 24408BromineHCID 699697HCID 699697, compound

Product 1

HCID 86698556HCID 86698556, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The solid (10 g, 49.60 mmol) from step 1 dissolved in acetic acid (70 mL) was added with Br2 (12.7 mL, 247.93 mmol) dropwise for 2 h. Then the reaction mixture was kept stirring at rt for 5.5 h. The resulting mixture was poured to ice water (1 L) and quenched with excess of NaHSO3 until the solution became clear with yellow suspension. The quenched solution was filtered to get title compound (13.52 g, 97.2%). 1H NMR (400 MHz, DMSO-d6) δ 1.07 (t, J=7.6 Hz, 3H), 2.36 (q, J=7.6 Hz, 2H), 7.80 (d, J=7.6 Hz, 1H), 7.84 (d, J=8.8 Hz, 1H), 9.50 (br s, 1H); 13C NMR (100 MHz, DMSO-d6) δ 10.1, 29.3, 117.3, 117.4, 119.0, 119.2, 121.0, 121.2, 128.4, 134.45, 134.49, 153.4, 155.9, 173.0;

Workup

  1. customquenched with excess of NaHSO3 until the solution
  2. filtrationThe quenched solution was filtered

Sources & evidence

ORD record
ord-a89b3c1bd3fe4b9b86fb30c84d6fd332
Source dataset
uspto-grants-2015_10
Patent number
US09155739B2

Reaction notes

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