Heptane → 2-(Bromomethyl)-4-chloro-1-fluorobenzene

HRID 1516877노트

반응식

HRID 1516877 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([CH3:8])[CH:7]=1.[Br:10]N1C(=O)CCC1=O.CCCCCCC.C1(=O)NC(=O)CC1>C(OC(=O)C)C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([CH:7]=1)[CH2:8][Br:10]

참가 물질

7

반응물 4

HCID 8900HeptaneHCID 11439SuccinimideHCID 67184N-bromobutanimideHCID 27251135-Chloro-2-fluorotoluene

생성물 1

HCID 27736262-(Bromomethyl)-4-chloro-1-fluorobenzene수율 104.8%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

5-Chloro-2-fluoro-toluene (100 g, 692 mmol) was dissolved in ethylacetate (300 ml) at 20° C. To this solution N-bromosuccinimide (147.7 g, 830 mmol) and dibenzoyl peroxide (2 g, 8.25 mmol) was added. The mixture was stirred at 80° C. for 3 hours. Heptane (300 ml) was added and the solution was cool to 0° C. whereupon succinimide precipitates. After filtration and washing with heptane, the residue was washed with water (1500 ml). The filtrate was concentrated in vacuo to dryness, yielding 162 grams of crude 5-chloro-2-fluoro-benzylbromide. Purification of the crude product (141 grams) was done by vacuum distillation at 99° C. and 33 mbar, this 5-chloro-2-fluoro-benzylbromide (99 grams, 75%). Purity according to GC is 87.1% a/a.

후처리

  1. customprecipitates
  2. filtrationAfter filtration
  3. washwashing with heptane
  4. washthe residue was washed with water (1500 ml)
  5. concentrationThe filtrate was concentrated in vacuo to dryness

출처 및 근거

ORD 기록
ord-2a0d8c765b974ba8aae5c5c5c2a8e6e7
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227623B2

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