Carbon tetrabromide → tert-Butyl 3-(bromomethyl)phenylcarbamate

HRID 546093

반응식

HRID 546093 반응식
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14]O)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:37]>O1CCCC1.C(#N)C>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][Br:37])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 14523557tert-Butyl (3-(hydroxymethyl)phenyl)carbamate

생성물 1

HCID 14523558tert-Butyl 3-(bromomethyl)phenylcarbamate수율 78%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매

실험 절차

The (3-hydroxymethyl-phenyl)-carbamic acid tert-butyl ester (1.67 g, 7.49 mmol) and triphenylphosphine (2.61 g, 9.96 mmol) were combined and dissolved in tetrahydrofuran (40 mL). Carbon tetrabromide (3.23 g, 9.74 mmol) was dissolved in acetonitrile (20 mL) and added dropwise to the reaction while stirring. After stirring for 5 h, the reaction was concentrated in vacuo to give a thick golden oil. Purification by flash column chromatography (Merck silica gel 60, 40-63 μm; 20% ethyl acetate/hexanes) afforded (3-bromomethyl-phenyl)-carbamic acid tert-butyl ester (1.52 g, 78%) as a white powder: H1-NMR (400 MHz, CDCl3) δ 1.53 (9H, s), 4.46 (2H, s), 6.47 (1H, bs), 7.06 (1H, d, J=7.2 Hz), 7.19-7.27 (2H, m), 7.51 (1H, s).

후처리

  1. additionadded dropwise to the reaction
  2. stirringAfter stirring for 5 h
  3. concentrationthe reaction was concentrated in vacuo
  4. customto give a thick golden oil
  5. customPurification by flash column chromatography (Merck silica gel 60, 40-63 μm; 20% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-5486c4aff0ed4f1195622eeb6518e583
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935699B2

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