Sulfuric Acid → 7-Bromomethylnaphthalene-1-carboxylic acid tert-butyl ester

HRID 496324Notes

Reaction equation

HRID 496324 reaction equation
[CH3:1][C:2](=[CH2:4])[CH3:3].[Br:5][CH2:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[C:14]2[C:17]([OH:19])=[O:18])=[CH:9][CH:8]=1.S(=O)(=O)(O)O>ClCCl>[C:2]([O:19][C:17]([C:14]1[C:15]2[C:10](=[CH:9][CH:8]=[C:7]([CH2:6][Br:5])[CH:16]=2)[CH:11]=[CH:12][CH:13]=1)=[O:18])([CH3:3])([CH3:1])[CH3:4]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 121243507-Bromomethylnaphthalene-1-carboxylic acid

Product 1

HCID 121243517-Bromomethylnaphthalene-1-carboxylic acid tert-butyl esterYield 88.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isobutylene was passed through a suspension of 7-bromomethylnaphthalene-1-carboxylic acid (10.4 g, 39.2 mmol) in dichloromethane (150 mL) in the presence of concentrated sulfuric acid (1 mL) for 3 hours, and then the mixture was stirred overnight. The resulting deep green solution was washed with a saturated solution of sodium hydrogen carbonate, dried (magnesium sulfate) and the solvent was removed under reduced pressure to give crude 7-bromomethylnaphthalene-1-carboxylic acid tert-butyl ester (11.2 g, 88.8%) as a deep green oil. This compound was directly used for the subsequent Michaelis-Becker alkylation without further purification.

Workup

  1. washThe resulting deep green solution was washed with a saturated solution of sodium hydrogen carbonate
  2. dry with materialdried (magnesium sulfate)
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4fec92ad74db4fd991e180866dc93688
Source dataset
uspto-grants-2005_09
Patent number
US06943267B1

Reaction notes

Loading…