Carbon tetrabromide → HCID 17951766, compound

HRID 1766125Notes

Reaction equation

HRID 1766125 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[S:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)=[N:13][C:12]=2[CH2:26]O)=[CH:5][C:4]=1[CH3:28].C(Br)(Br)(Br)[Br:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:30][CH2:26][C:12]1[N:13]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[S:15][C:11]=1[CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([CH3:28])[CH:5]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 21109454HCID 21109454, compound

Product 1

HCID 17951766HCID 17951766, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 100 ml round-bottom flask equipped with a magnetic stir-bar and N2 inlet was added {5-[2-(4-Methoxy-3-methyl phenyl)ethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl}methanol (0.708 g, 1.74 mmoles, 1 eq), CH2Cl2 (20 ml), carbon tetrabromide (0.634 g, 1.91 mmoles, 1.1 eq) and triphenylphosphine (0.501 g, 1.91 mmoles, 1.1 eq) in that order. The reaction was stirred overnight at which time it was diluted with CH2Cl2 and washed with H2O, brine, dried over Na2SO4, concentrated in vacuo and purified via silica gel chromatography to yield 573 mg (70%) of product.

Workup

  1. customTo a 100 ml round-bottom flask equipped with a magnetic stir-bar and N2 inlet
  2. washwashed with H2O, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. custompurified via silica gel chromatography

Sources & evidence

ORD record
ord-974982b06add4cb0b3c8f72c0d28dc56
Source dataset
uspto-grants-2007_06
Patent number
US07229998B2

Reaction notes

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