Butyl bromide → (2'-Methoxyethoxymethoxy-[1,1';3'1'']terphenyl-5'-yloxy)butane

HRID 1743436Notes

Reaction equation

HRID 1743436 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][C:11]([OH:20])=[CH:10][C:9]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:34][CH2:35][CH2:36][CH3:37]>CN(C=O)C.O.CCOC(C)=O>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][C:11]([O:20][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:10][C:9]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 222375693,5-Diphenyl-4-[(2-methoxyethoxy)methoxy]-phenol

Product 1

HCID 131722493(2'-Methoxyethoxymethoxy-[1,1';3'1'']terphenyl-5'-yloxy)butaneYield 92.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 2′-methoxyethoxymethoxy-[1,1′;3′,1″]terphenyl-5′-ol (0.240 g, 0.685 mmol) in DMF (10 mL) at room temperature was added K2CO3 (0.123 g, 0.890 mmol) followed by dropwise addition of 1-bromobutane (0.147 mL, 1.37 mmol). The reaction mixture was then heated to 60° C. After 4 days at this temperature, the resulting solution was diluted with H2O (10 mL) and excess EtOAc (100 mL). The organic layer was washed with 1 N HCl (10 mL), sat. aq. NaHCO3 (10 mL), and brine (10 mL) and then dried (MgSO4). After concentration, the residue was purified by preparatory plate chromatography (20% EtOAc/petroleum ether) to afford the product (0.257 g, 92%) as a solid; 1H NMR (CDCl3) δ 0.97 (t, J=8.1 Hz, 3H), 1.46–1.57 (m, 2H), 1.72–1.82 (m, 2H), 2.80 (t, J=5.6 Hz, 2H), 2.95 (t, J=5.6 Hz, 2H), 3.17 (s, 3H), 3.99 (t, J=6.9 Hz, 2H), 4.37 (s, 2H), 6.87 (s, 2H), 7.28–7.46 (m, 6H), 7.58 (d, J=7.5 Hz, 4H); mass spectrum [(+) ESI], m/z 429 (M+Na)+.

Workup

  1. washThe organic layer was washed with 1 N HCl (10 mL), sat. aq. NaHCO3 (10 mL), and brine (10 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationAfter concentration
  4. customthe residue was purified by preparatory plate chromatography (20% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-4d65cafc25e6455f9ae725451ffc48f6
Source dataset
uspto-grants-2006_03
Patent number
US07008636B2

Reaction notes

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