Triphenylphosphine → 5-(Bromomethyl)-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole

HRID 2103421Notes

Reaction equation

HRID 2103421 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[S:5][C:6]=1[CH2:7]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:38]N1C(=O)CCC1=O>C1COCC1>[Br:38][CH2:7][C:6]1[S:5][C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[N:3][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 2783005(4-Methyl-2-(4-(trifluoromethyl)phenyl)-1,3-thiazol-5-yl)methanol

Product 1

HCID 27946295-(Bromomethyl)-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazoleYield 83.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cool (10° C.) a solution of [4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methanol (Example 2, 753 mg, 3 mmol) in THF (12 mL) add triphenylphosphine (864 mg, 3.3 mmol) followed by freshly recrystallized N-bromosuccinimide (587 mg, 3.3 mmol). On complete addition, remove the cold bath and stir continuously for 45 min. Concentrate the resulting mixture under vacuum and purify the residue by flash chromatography (elute with 10% ethyl acetate/10% dichloromethane in heptane) to give the title compound as an orange solid (846 mg).

Workup

  1. additionOn complete addition
  2. customremove the cold bath
  3. concentrationConcentrate the resulting mixture under vacuum
  4. custompurify the residue
  5. washby flash chromatography (elute with 10% ethyl acetate/10% dichloromethane in heptane)

Sources & evidence

ORD record
ord-93ee86fc6df34e0eb204087b5d2aba55
Source dataset
uspto-grants-2009_08
Patent number
US07576109B2

Reaction notes

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