Potassium Carbonate → (4-Fluorophenyl)methyl 5-bromo-2-{[(4-fluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)benzoate

HRID 2204688Notes

Reaction equation

[Br:1][C:2]1[C:3]([CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].C(=O)([O-])[O-].[K+].[K+].[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1>CN(C)C=O>[Br:1][C:2]1[C:3]([CH2:12][N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)=[CH:4][C:5]([O:11][CH2:30][C:29]2[CH:32]=[CH:33][C:26]([F:25])=[CH:27][CH:28]=2)=[C:6]([CH:10]=1)[C:7]([O:9][CH2:30][C:29]1[CH:32]=[CH:33][C:26]([F:25])=[CH:27][CH:28]=1)=[O:8]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 5-bromo-2-hydroxy-4-(4-morpholinylmethyl)benzoic acid (may be prepared as described in Description 5; 720 mg, 2.28 mmol) in N,N-dimethylformamide (10 ml) was added potassium carbonate (1102 mg, 7.97 mmol) and 4-fluorobenzyl bromide (0.62 ml, 5.01 mmol). The mixture was heated at 50° C. for 2 hours, cooled and the solvent removed in vacuo. The residue was partitioned between water (10 ml) and ethyl acetate (15 ml). The organic layer was separated, washed further with water (2×5 ml), dried (MgSO4) and the solvent removed in vacuo to give a residue. Purification by column (SiO2, 6:1-1:1 cyclohexane/ethyl acetate) gave the product as a pale yellow oil. 544 mg.

Workup

temperaturecooled
customthe solvent removed in vacuo
customThe residue was partitioned between water (10 ml) and ethyl acetate (15 ml)
customThe organic layer was separated
washwashed further with water (2×5 ml)
dry with materialdried (MgSO4)
customthe solvent removed in vacuo
customto give a residue
customPurification by column (SiO2, 6:1-1:1 cyclohexane/ethyl acetate)

Sources & evidence

ORD record: ord-72d6329311504e2386ee3518c1318dfc
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365551B2

Reaction notes

Loading…