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Triethylamine → 5-Tert-butyl-2-methoxy-3-nitro-benzyl methanesulphonate

HRID 2360514
Notes
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Reaction equation

HRID 2360514 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:15]([O-:17])=[O:16])[C:8]([O:13][CH3:14])=[C:9]([CH2:11][OH:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl>[CH3:25][S:26]([O:12][CH2:11][C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=[C:7]([N+:15]([O-:17])=[O:16])[C:8]=1[O:13][CH3:14])(=[O:28])=[O:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58493934(5-Tert-butyl-2-methoxy-3-nitrophenyl)methanol

Product 1

HCID 584939545-Tert-butyl-2-methoxy-3-nitro-benzyl methanesulphonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3.43 g (5-tert-butyl-2-methoxy-3-nitro-phenyl)-methanol are dissolved in 30 ml dichloromethane, combined with 2.39 ml of triethylamine and cooled to 0° C. 1.2 g of methanesulphonic acid chloride are added dropwise and the mixture is stirred for 2 hours. Then it is diluted with dichloromethane and washed 3 times with water and once with saturated aqueous sodium chloride solution. After drying with magnesium sulphate the solvents are eliminated in vacuo and the product thus obtained is further reacted directly.

Workup

  1. washwashed 3 times with water
  2. dry with materialAfter drying with magnesium sulphate the solvents
  3. customthe product thus obtained
  4. customis further reacted directly

Sources & evidence

ORD record
ord-e99786ebe4314e7fb79c507b25c96553
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08686022B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes