Carbon tetrabromide → N-(2-Bromomethyl-phenyl)-N-methyl-methanesulfonamide

HRID 472488ノート

反応式

HRID 472488 の反応式
O[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]([CH3:14])[S:10]([CH3:13])(=[O:12])=[O:11].C(Br)(Br)(Br)[Br:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:16][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]([CH3:14])[S:10]([CH3:13])(=[O:12])=[O:11]

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 66756625HCID 66756625、化合物

生成物 1

HCID 67478774N-(2-Bromomethyl-phenyl)-N-methyl-methanesulfonamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

196 d) To a stirred mixture of N-(2-hydroxymethyl-phenyl)-N-methyl-methanesulfonamide (0.90 g, 4.2 mmol) and carbon tetrabromide (2.40 g, 7.24 mmol) in dry tetrahydrofuran (50 mL) was added triphenylphosphine (1.90 g, 7.23 mmol). The mixture was stirred at room temperature for 18 hours. The volatiles were evaporated under reduced pressure. The residue was triturated with ethyl acetate (30 mL) then filtered and evaporated under reduced pressure. The residue was purified via chromatography (silica gel column 40 g 5%→100% ethyl acetate:hexane). N-(2-Bromomethyl-phenyl)-N-methyl-methanesulfonamide was isolated as pale yellow solid (0.86 g, 74%), 1H NMR (400 MHz, CDCl3, δ, ppm): 7.57-7.52 (m, 1H), 7.41-7.34 (m, 2H), 7.30-7.25 (m, 1H), 5.29-4.30 (br m, 2H), 3.34 (s, 3H), 2.98 (s, 3H).

後処理

  1. customThe volatiles were evaporated under reduced pressure
  2. customThe residue was triturated with ethyl acetate (30 mL)
  3. filtrationthen filtered
  4. customevaporated under reduced pressure
  5. customThe residue was purified via chromatography (silica gel column 40 g 5%→100% ethyl acetate:hexane)

出典と根拠

ORDレコード
ord-bc310a28f6624ecf8784ea9dc550e32b
出典データセット
uspto-grants-2014_01
特許番号
US08633173B2

反応ノート

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