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

HRID 472488Notes

Reaction equation

HRID 472488 reaction equation
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]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 66756625HCID 66756625, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-bc310a28f6624ecf8784ea9dc550e32b
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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