Bromine → HCID 117664174, compound

HRID 2199491Notes

Reaction equation

HRID 2199491 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9](/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:4]=1[C:5]([O:7][CH3:8])=[O:6].[Br:23]Br>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([Br:23])=[C:9](/[CH:15]=[CH:16]/[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 24408BromineHCID 72713558HCID 72713558, compound

Product 1

HCID 117664174HCID 117664174, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve compound 6 (13.0 g, 0.046 mol) CH2Cl2 (150 ml), add bromine (8.1 g, 0.050 mol) dropwise at room temperature, react at room temperature for 1 h, after completion of the reaction, wash the organic layer successively with water, saturated NaHCO3 solution and brine, dry the organic solution over anhydrous MgSO4. Filter the solution and evaporate the solvent, redissolve the residue, feed the solution to a silica gel column, evaporate the solvent in the eluent to obtain a white solid (15.1 g, 87%). 1H NMR (400 MHz, CDCl3): 3.80 (s, 3H), 3.86 (s, 3H), 3.93 (s, 3H), 639 (d, J=15.6 Hz, 1H), 6.50 (s, 1H), 70 (d, J=15.6 Hz, 1H), 7.29 (t, J=7.6 Hz, 1H), 7.37 (t, J=7.6 Hz, 2H), 7.49 (d, J=7.6 Hz, 2H).

Workup

  1. customreact at room temperature for 1 h
  2. customafter completion of the reaction
  3. washwash the organic layer successively with water, saturated NaHCO3 solution and brine
  4. dry with materialdry the organic solution over anhydrous MgSO4
  5. filtrationFilter the solution
  6. customevaporate the solvent
  7. dissolutionredissolve the residue
  8. customevaporate the solvent in the eluent

Sources & evidence

ORD record
ord-e04b0a64f7e2476f856bee324f1c0020
Source dataset
uspto-grants-2016_06
Patent number
US09359298B2

Reaction notes

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