Methanol → HCID 22246779, compound

HRID 890765Notes

Reaction equation

HRID 890765 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([CH:16]=[CH:17][CH:18]=1)[CH2:10][NH:11][S:12]([CH3:15])(=[O:14])=[O:13].CO>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]([CH:16]=[CH:17][CH:18]=1)[CH2:10][NH:11][S:12]([CH3:15])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 1484598HCID 1484598, compound

Product 1

HCID 22246779HCID 22246779, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of BBr3 (1.0 M in CH2Cl2, 111 mL, 111 mmol) was slowly added to a solution of N-(3-methoxy-benzyl)-methanesulfonamide (12.000 g, 55.7 mmol) in CH2Cl2 (200 mL) at 0° C. The reaction was warmed to room temperature and was stirred for 4 h. Methanol (100 mL) was cautiously added and the solution was concentrated in vacuo. Flash chromatography (1:1 hexanes:EtOAc) provided N-(3-hydroxy-benzyl)-methanesulfonamide (11.50 g). 1H NMR (400 MHz, CDCl3) δ 7.20 (m, 1H), 6.84 (m, 2H), 6.77 (m, 1H), 4.83 (bs, 1H), 4.24 (s, 2H), 2.86 (s, 3H); MS 201 (M+).

Workup

  1. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-3f22571552444697b264c739cfea6854
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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