Pyridine → HCID 20405953, compound

HRID 2164221Notes

Reaction equation

HRID 2164221 reaction equation
CC1C=CC=CC=1CC([Cl:11])=O.[Br:12][CH:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][Br:24])[C:14](Cl)=[O:15].[C:25]([OH:29])([CH3:28])([CH3:27])[CH3:26].[N:30]1C=CC=CC=1>CCOCC>[ClH:11].[CH:13]1([C:14]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:15])[CH:17]2[CH:18]([CH2:19][CH2:20][CH2:21][CH2:22]2)[CH2:23][NH:30]1.[Br:12][CH:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][Br:24])[C:14]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:15]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6386tert-ButanolHCID 2760632o-Tolyl-acetyl chlorideHCID 20405960HCID 20405960, compound

Product 2

HCID 20405953HCID 20405953, compoundHCID 20405958HCID 20405958, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

The t-butyl octahydro-1H-isoindole-1-carboxylate hydrochloride is prepared as follows. Following a procedure given in Gazz. Chim. Ital, 106, 65(1976), 56 g of (2-methylphenyl)acetyl chloride is converted to 2-bromo-(2-bromomethylphenyl)acetyl chloride. This is added dropwise to a solution of 78.6 g of t-butyl alcohol in 120 ml of ether and cooled at 0° C. Finally 26.4 g of pyridine is added. After a few minutes, the precipitated solids are filtered and washed with ether. The filtrate is washed successively with water and dilute sodium bicarbonate solution dried and concentrated at reduced pressure. t-Butyl 2-bromo-(2-bromomethylphenyl)acetate is obtained as an oil of sufficient purity for further use by chromatography over silica gel, eluting with a 4:1 hexane/ethyl acetate mixture.

Workup

  1. waitAfter a few minutes
  2. filtrationthe precipitated solids are filtered
  3. washwashed with ether
  4. washThe filtrate is washed successively with water and dilute sodium bicarbonate solution
  5. customdried
  6. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-b78d7624f0f94d209e8000fff06fe7fc
Source dataset
uspto-grants-1985_03
Patent number
US04503043

Reaction notes

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