Carbon tetrabromide → Methyl 3-azidomethyl-5-fluoromethylbenzoate

HRID 473237노트

반응식

HRID 473237 반응식
[F:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH2:13]O)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[N-:15]=[N+:16]=[N-:17].[Na+].C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C(N(CC)CC)C>[N:15]([CH2:13][C:11]1[CH:10]=[C:5]([CH:4]=[C:3]([CH2:2][F:1])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=[N+:16]=[N-:17]

참가 물질

7

반응물 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 67253567Methyl 3-fluoromethyl-5-hydroxymethylbenzoate

생성물 1

HCID 86671517Methyl 3-azidomethyl-5-fluoromethylbenzoate수율 53%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

Methyl 3-fluoromethyl-5-hydroxymethylbenzoate (34) (2.30 g, 11.6 mmol) was dried for 24 hours. Sodium azide (3.77 g, 58.1 mmol), carbon tetrabromide (4.24 g, 12.1 mmol), and triphenylphosphine (3.66 g, 13.9 mmol) were dried for 48 hours. Under Ar atmosphere, these were mixed with triethylamine (3.6 mL), dissolved in DMF (88 mL), and stirred for 93 hours at a room temperature. TLC was used to confirm the progress of the reaction. Then, the mixture was extracted with EtOAc. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to remove the solvent. The residue was purified by neutral silica gel column chromatography (hexane:EtOAc=10:1) to isolate methyl 3-azidomethyl-5-fluoromethylbenzoate (35) (1.37 g, 53%) as a pale yellow oil.

후처리

  1. customthe progress of the reaction
  2. extractionThen, the mixture was extracted with EtOAc
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by neutral silica gel column chromatography (hexane:EtOAc=10:1)

출처 및 근거

ORD 기록
ord-7cb982ea968b4d24bcc82fc392c3b391
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633304B2

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