Bromine → HCID 9996412, compound

HRID 1956959Notes

Reaction equation

HRID 1956959 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH:16]([CH3:18])[CH3:17])=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[CH:8][CH:7]([CH3:15])[CH2:6]2.[Br:19]Br>ClCCl>[Br:19][C:8]1[CH:7]([CH3:15])[CH2:6][C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[C:4]=2[CH:16]([CH3:18])[CH3:17])[CH:9]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 10014812HCID 10014812, compound

Product 1

HCID 9996412HCID 9996412, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Compound 12 (3.00 g, 12.2 mmol) was dissolved in 20 mL of dichloromethane and bromine (1.95 g, 12.2 mmol) in 5 ml of dichloromethane was added dropwise with stirring over a period of 15 min. The solvent was evaporation and the residue was taken up in 15 ml of DMF. The DMF solution was warmed to 50°-60° C. for 1 h. The reaction mixture was poured onto ice and stirred. The solid product was filtered, dried and recrystallized from a concentrated petroleum ether solution to give 3.60 g (11.1 mmol, 91%) of 13 as nearly colorless microcrystalline plates: mp 71°-72° C.; 1H NMR 1.09 (d, J=6.95, 3 H) , 1.32 (d, J=7.2 Hz, 6 H), 2.4-3.2 (m, 3 H), 3.49 (m, 1 H), 3.80 (s, 3 H), 3.82 (s, 3H), 6.43 (s, 1 H), 6.64 (s, 1H). Anal. (C16H21BrO2) C, H.

Workup

  1. customevaporation
  2. temperatureThe DMF solution was warmed to 50°-60° C. for 1 h
  3. additionThe reaction mixture was poured onto ice
  4. stirringstirred
  5. filtrationThe solid product was filtered
  6. customdried
  7. customrecrystallized from a concentrated petroleum ether solution

Sources & evidence

ORD record
ord-cc0541be158e40a79760ccec8cc6c7aa
Source dataset
uspto-grants-1998_07
Patent number
US05780675

Reaction notes

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