Hydrogen Bromide → 5-(4-hydroxyphenyl)-2,2-dimethyl-4-(4-(quinolin-2-ylmethoxy)phenyl)furan-3(2H)-one

HRID 1776285Notes

Reaction equation

HRID 1776285 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11](=[O:16])[C:10]=2[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]=3)=[CH:19][CH:18]=2)=[CH:5][CH:4]=1.Br>C1COCC1.O>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([CH3:14])([CH3:15])[C:11](=[O:16])[C:10]=2[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]=3)=[CH:19][CH:18]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 445944685-(4-methoxyphenyl)-2,2-dimethyl-4-(4-(quinolin-2-ylmethoxy)phenyl)furan-3(2H)-one

Product 1

HCID 593548675-(4-hydroxyphenyl)-2,2-dimethyl-4-(4-(quinolin-2-ylmethoxy)phenyl)furan-3(2H)-oneYield 8.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred 0° C. solution of 5-(4-methoxyphenyl)-2,2-dimethyl-4-(4-(quinolin-2-ylmethoxy)phenyl)furan-3(2H)-one (1.0 g, 2.61 mmol) in THF (10 mL), aqueous HBr (908 mg, 5.2 mmol) was added under a nitrogen atmosphere. The reaction mixture was then stirred for 12 h at RT, diluted with water and extracted with hexane (2×50 mL). The organic layers were concentrated in vacuo to afford 5-(4-hydroxyphenyl)-2,2-dimethyl-4-(4-(quinolin-2-ylmethoxy)phenyl)furan-3(2H)-one (100 mg) as a white solid. 1H NMR (500 MHz, d6-DMSO): δ 10.25 (s, 1 H), 8.48 (d, J=7.8 Hz, 1 H), 8.16-8.00 (m, 2 H), 7.95 (t, J=7.8 Hz, 1 H), 7.72 (t, J=7.8 Hz, 1 H), 7.63 (t, J=7.2 Hz, 1 H), 7.56 (d, J=7.2 Hz, 2 H); 7.18 (d, J=7.2 Hz, 2 H), 7.12 (d, J=7.2 Hz, 2 H), 6.89 (d, J=7.6 Hz, 2 H), 5.32 (s, 2 H), 1.37 (s, 6 H). MS: M+H: m/z=438.2; and LC MS: 88%, (Condition-H).

Workup

  1. extractionextracted with hexane (2×50 mL)
  2. concentrationThe organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-197d4b67b07e40ddb125f97d3f3f1918
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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