Carbon tetrabromide → HCID 66906229, compound

HRID 1689765Notes

Reaction equation

HRID 1689765 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14]O)=[C:12]([CH:16]([CH3:18])[CH3:17])[N:11]=[N:10]1.C(Br)(Br)(Br)[Br:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:20][CH2:14][C:13]1[N:9]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])[N:10]=[N:11][C:12]=1[CH:16]([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 45790389(1-(2,6-dichlorophenyl)-4-isopropyl-1H-1,2,3-triazol-5-yl)methanol

Product 1

HCID 66906229HCID 66906229, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (1-(2,6-dichlorophenyl)-4-isopropyl-1H-1,2,3-triazol-5-yl)methanol (3.0 g, 0.01048 mol) and CBr4 in CH2Cl2 (15 ml) is added a solution of triphenylphosphine (3.50 g, 0.01334 mol) in CH2Cl2 (10 ml) at 0° C. Stir the solution for 4 h at room temperature and concentrate in vacuo to give crude product. Purify by column chromatography over silica gel eluting with 7:3 hexane/ethyl acetate to give 3.0 g (82%) of the title compound. ES/MS m/e (79Br/81Br) 348/350 [M+H]+.

Workup

  1. concentrationconcentrate in vacuo
  2. customto give crude product
  3. customPurify by column chromatography over silica gel eluting with 7:3 hexane/ethyl acetate

Sources & evidence

ORD record
ord-828ed5b1fff4470db96c84739ad9ec87
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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