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

HRID 472488노트

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HRID 472488 반응식
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]

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 66756625HCID 66756625, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-bc310a28f6624ecf8784ea9dc550e32b
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633173B2

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