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

HRID 2103421

反応式

HRID 2103421 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-93ee86fc6df34e0eb204087b5d2aba55
出典データセット
uspto-grants-2009_08
特許番号
US07576109B2

関連ノート

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