Benzyl Bromide → 6-Fluoro-7-benzyloxychroman-4-one

HRID 1384321노트

반응식

HRID 1384321 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][CH2:7][CH2:6][C:5]2=[O:13].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:8][CH2:7][CH2:6][C:5]2=[O:13]

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 211866006-fluoro-7-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one

생성물 1

HCID 211865906-Fluoro-7-benzyloxychroman-4-one수율 73%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of 6-fluoro-7-hydroxychroman-4-one (the compound of Preparation 29, 0.93 g, 5.11 mmol), benzyl bromide (0.61 mL, 5.13 mmol), potassium carbonate (1.41 g, 10.2 mmol) in acetone (100 mL) was stirred at ambient temperature overnight. The mixture was cooled, filtered, and concentrated to a yellow solid. This residue was recrystallized from ethyl acetate/ether to give 1.02 g (73%) of 6-fluoro-7-benzyloxychroman-4-one in two crops as cream white crystals which had: mp 155-156° C.; NMR δ7.58 (d, J=11 Hz, 1 H), 7.46-7.33 (m, 5 H), 6.54 (d, J=6.7 Hz, 1 H), 5.16 (d, 2 H), 4.50 (t, J=6.4 Hz, 2 H), 2.75 (t, J=6.4 Hz, 2 H). Analysis calculated for C16H13FO2: C, 70.58; H, 4.81. Found: C, 70.45; H, 4.80.

후처리

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated to a yellow solid
  4. customThis residue was recrystallized from ethyl acetate/ether

출처 및 근거

ORD 기록
ord-6835b40a682e40d0a3c9b9a1b3ad3184
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06258827B1

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