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

HRID 337659노트

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HRID 337659 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2abfda4e64324c5b9869a32e5436db68
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889714B2

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