4-Bromophenacyl bromide → HCID 58934678, compound

HRID 855163Notes

Reaction equation

HRID 855163 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]([F:15])([F:14])[F:13])[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:5]2.[Br:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:31])[CH2:29]Br)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:31])[CH2:29][O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[O:8][CH:7]([C:12]([F:15])([F:13])[F:14])[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:5]3)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 11430Potassium CarbonateHCID 58934503HCID 58934503, compound

Product 1

HCID 58934678HCID 58934678, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

The mixture of ethyl 6-hydroxyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate (1.0 g, 3.47 mmol), 2-(4-bromophenyl)-2-oxoethyl bromide (0.96g, 3.47mmol) and potassium carbonate (0.96 g, 6.94 mmol) in 4 mL of dry DMF was heated to 70° C. and shaken for two hrs, then at room temperature overnight. The solid was filtered, and washed with ethyl acetate. The combined organic phases were washed with brine, and then dried over anhydrous magnesium sulfate. After removing the volatiles, the residue was purified on silica gel column with 1:9 EtOAc/hexane. It gave 0.65 g of light yellow solid (38.6%). M.P.=130.5-131.5° C. 1HNMR (CDCl3/400 MHz) 7.86(m, 1H), 7.83(m, 1H) 7.65(m, 1H), 7.63-7.62(m, 2H), 6.89-6.88(m, 2H), 6.77(m, 1H),5.64(q, J=6.8 Hz, 1H, ), 5.16(s, 2H), 4.33-4.26(m, 2H), 1.33(t, J=7.2 Hz, 3H). 13C NMR (CDCl3/300 MHz), 193.8, 163.9, 153.3, 148.2, 136.8, 133.3, 132.5, 129.9, 129.5, 123.6 (q, J=287.9 Hz), 119.9, 119.8, 117.8, 117.1, 115.1, 71.8, 70.8(q, J=32.8 Hz), 61.7, 14.4. 19F(CDCl3/400 MHz) −78.72(d, J=6.8 Hz). LC-MS: 484.9 (M+1, 100), 486.9(M+3, 100). Purity =95%. HRMS (ES+) m/z calcd for (C21H16BrF3O5) 502.0471(M+NH4), 504.0454 (M+NH4+2), found 502.0484, 504.0492.

Workup

  1. customat room temperature
  2. customovernight
  3. filtrationThe solid was filtered
  4. washwashed with ethyl acetate
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter removing the volatiles
  8. customthe residue was purified on silica gel column with 1:9 EtOAc/hexane

Sources & evidence

ORD record
ord-13bdfd1e108e4459a48f51f95394d6a5
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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