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

HRID 546093

反応式

HRID 546093 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 14523558tert-Butyl 3-(bromomethyl)phenylcarbamate収率 78%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-5486c4aff0ed4f1195622eeb6518e583
出典データセット
uspto-grants-2011_05
特許番号
US07935699B2

関連ノート

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