1192474-21-7 → 1192474-22-8

HRID 541932Notes

Reaction equation

HRID 541932 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=[C:6]([CH2:8][OH:9])[CH:7]=1>ClCCCl.[O-2].[Mn+4].[O-2]>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16])[CH:5]=[C:6]([CH:8]=[O:9])[CH:7]=1

Participants

4

Reactant 1

HCID 579619961192474-21-7

Product 1

HCID 579619971192474-22-8Yield 82.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of tert-butyl [3-bromo-5-(hydroxymethyl)phenyl]carbamate (13.3 g, 44.2 mmol) and manganese(IV) oxide (19.2 g, 221 mmol) in 1,2-dichloroethane (88 mL) was stirred at 80° C. for 3 h. The reaction mixture was treated with additional manganese(IV) oxide (11.5 g, 132 mmol) and stirred at 80° C. for 16 h. The reaction mixture was filtered over celite (2×) and washed with dichloromethane. The filtrate was concentrated to give the desired product (10.9 g, 82% for 2 steps) as a white solid. LCMS for C12H14BrNO3Na (M+Na)+: m/z=321.9, 323.9.

Workup

  1. filtrationThe reaction mixture was filtered over celite (2×)
  2. washwashed with dichloromethane
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-78e75f9ac2384f84a14f7561292954c2
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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