Sodium Iodide → 4-[4-(2-Benzyloxy-4-ethyl-phenoxy)-3-fluoro-phenoxy]-butyric acid ethyl ester

HRID 1023972Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:23]=[C:22]([CH2:24][CH3:25])[CH:21]=[CH:20][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=1[F:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Na+].[I-].Br[CH:35]([CH2:41][CH3:42])[C:36]([O:38][CH2:39][CH3:40])=[O:37].C([N+](CCCC)(CCCC)CCCC)CCC.[NH4+].[Cl-]>CC(C)=O.O>[CH2:39]([O:38][C:36](=[O:37])[CH2:35][CH2:41][CH2:42][O:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:10]2[CH:20]=[CH:21][C:22]([CH2:24][CH3:25])=[CH:23][C:9]=2[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:13]([F:19])[CH:14]=1)[CH3:40]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-[2-(benzyloxy)-4-ethylphenoxy]-3-fluorophenol (0.30 mmol; 100 mg) in dry acetone (2 mL), under argon, were added potassium carbonate (0.35 mmol; 49 mg), NaI (0.06 mmol; 9 mg) and ethyl bromobutyrate (0.35 mmol; 51 μL). The reaction was stirred 14 hours at 60° C. Water (100 μL) and tetrabutylammonium hydroxyde (0.03 mmol; 8 mg) were added and the mixture was stirred 16 hours at 60° C. The reaction was hydrolysed with NH4Cl sat. (5 mL) and extracted with ethyl acetate (3*3 mL). Combined organic phases were dried over Na2SO4, concentrated in vacuo. The title compound (100 mg; 0.22 mmol; 75%) was obtained as a yellow oil, after purification by preparative TLC (cyclohexane/ethyl acetate: 7/3).

Workup

stirringthe mixture was stirred 16 hours at 60° C
extractionextracted with ethyl acetate (3*3 mL)
dry with materialCombined organic phases were dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-97b5beb9de2e4f01b6c943fdefa26c35
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722746B2

Reaction notes

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