Water → HCID 58913074, compound

HRID 1296680Notes

Reaction equation

HRID 1296680 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:27][CH:26]=3)=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[C:9](=[O:13])[O:10]2)=[CH:5][CH:4]=1.[Br:38]Br.O>CC(O)=O>[Br:38][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[O:2][CH3:1])[O:10][C:9](=[O:13])[C:8]([C:14]1[CH:15]=[CH:16][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:18][CH:19]=1)=[C:7]2[CH2:24][C:25]1[CH:26]=[CH:27][C:28]([O:31][C:32](=[O:37])[C:33]([CH3:34])([CH3:36])[CH3:35])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408Bromine2×HCID 58913114HCID 58913114, compound

Product 1

HCID 58913074HCID 58913074, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2,2-dimethyl-propionic acid 4-(7-methoxy-2-oxo-3-(4-trifluoromethyl-phenyl)-2H-chromen-4-ylmethyl)-phenyl ester from step C (820 mg, 1.61 mmol) and Br2 (83 μL, 1.61 mmol) in AcOH (15 mL) was stirred at room temperature for 16 h. Another portion of Br2 (80 μL, 1.55 mmol) was added, and stirring was continued for 6 h. The mixture was poured into H2O, and the aqueous layer was extracted with CH2Cl2 (2×). The combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo. The residual orange solid was crystallized from CH2Cl2/hexane to afford the desired compound as a white solid (710 mg, 75%). 1H NMR (300 MHz, CDCl3) δ 7.67 (s, 1H), 7.65 (d, J=8.5 Hz, 2H), 7.38 (d, J=8.5 Hz, 2H), 7.07–6.94 (m, 4H), 6.89 (s, 1H), 4.01 (s, 2H), 3.98 (s, 3H), 1.35 (s, 9H); MS (ESI) m/z 588.8 (M+H)+; HPLC tR 7.78 min.

Workup

  1. stirringstirring
  2. waitwas continued for 6 h
  3. extractionthe aqueous layer was extracted with CH2Cl2 (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residual orange solid was crystallized from CH2Cl2/hexane

Sources & evidence

ORD record
ord-1f2a9e5160ae4513b23881b2318f0b47
Source dataset
uspto-grants-2007_07
Patent number
US07247646B2

Reaction notes

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