Imidazole → Methyl 3-bromo-5-(iodomethyl)-4-methylbenzoate

HRID 337659ノート

反応式

HRID 337659 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:20]I.N1C=CN=C1.[Br:27][C:28]1[CH:29]=[C:30]([CH:35]=[C:36]([CH2:39]O)[C:37]=1[CH3:38])[C:31]([O:33][CH3:34])=[O:32]>ClCCl>[Br:27][C:28]1[CH:29]=[C:30]([CH:35]=[C:36]([CH2:39][I:20])[C:37]=1[CH3:38])[C:31]([O:33][CH3:34])=[O:32]

参加物

6

反応物 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 66896191Methyl 3-bromo-5-(hydroxymethyl)-4-methylbenzoate

生成物 1

HCID 66896553Methyl 3-bromo-5-(iodomethyl)-4-methylbenzoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a dichloromethane (0.05 M) solution of triphenylphosphine (1.1 eq) was added iodine (1.1 eq.). The resulting orange-yellow suspension was stirred at RT for 30 min before imidazole (1.2 eq.) and finally methyl 3-bromo-5-(hydroxymethyl)-4-methylbenzoate (1 eq.) from the previous step were added. The now pale yellow solution was stirred at RT for another 30 min. The volatiles were removed in vacuo and the residue was triturated with a 1:1 (v/v) mixture of hexanes and ether. The insolubles were then removed via filtration through a pad of silica gel. Concentration of the filtrate in vacuo afforded the title compound as a white solid.

後処理

  1. additionwere added
  2. customThe volatiles were removed in vacuo
  3. customthe residue was triturated with a 1:1 (v/v) mixture of hexanes and ether
  4. customThe insolubles were then removed via filtration through a pad of silica gel

出典と根拠

ORDレコード
ord-2abfda4e64324c5b9869a32e5436db68
出典データセット
uspto-grants-2014_11
特許番号
US08889714B2

反応ノート

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