1,3-Dibromopropane → Ethyl 4'-(3-bromopropoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate

HRID 253484Notes

Reaction equation

HRID 253484 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4]Br.C(=O)([O-])[O-].[K+].[K+].[OH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][CH:20]=2)=[CH:15][C:14]=1[C:30]1[CH:39]=[CH:38][C:37]2[C:36]([CH3:41])([CH3:40])[CH2:35][CH2:34][C:33]([CH3:43])([CH3:42])[C:32]=2[CH:31]=1>C(C(C)=O)C>[Br:1][CH2:2][CH2:3][CH2:4][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[CH:21][C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:24]=2)=[CH:15][C:14]=1[C:30]1[CH:39]=[CH:38][C:37]2[C:36]([CH3:41])([CH3:40])[CH2:35][CH2:34][C:33]([CH3:42])([CH3:43])[C:32]=2[CH:31]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 57552328Ethyl 4'-hydroxy-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate

Product 1

HCID 66856107Ethyl 4'-(3-bromopropoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylateYield 55.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

320 μl (3.14 mmol) of 1,3-dibromopropane and 440 mg (3.18 mmol) of potassium carbonate are added to a solution of 900 mg (2.1 mmol, 1 eq) of ethyl 4′-hydroxy-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate in 30 ml of methyl ethyl ketone. The reaction mixture is stirred overnight at room temperature and then for 1 day at reflux. The medium is cooled to room temperature and then filtered. The filtrate is evaporated and the residue is purified by chromatography on silica gel (eluent: 90/10 heptane/ethyl acetate). 640 mg of ethyl 4′-(3-bromopropoxy)-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate are obtained in the form of a white solid (yield=55%).

Workup

  1. temperaturefor 1 day at reflux
  2. temperatureThe medium is cooled to room temperature
  3. filtrationfiltered
  4. customThe filtrate is evaporated
  5. customthe residue is purified by chromatography on silica gel (eluent: 90/10 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-171ed02dcc294a2e9f0dbfa82aaf68ec
Source dataset
uspto-grants-2011_01
Patent number
US07872026B2

Reaction notes

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