Sodium hydride → tert-Butyl (4-tert-butyl-3-fluorophenoxy)acetate

HRID 1350822Notes

Reaction equation

[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[F:14])([CH3:6])([CH3:5])[CH3:4].Br[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:9][C:8]=1[F:14])([CH3:6])([CH3:4])[CH3:5]

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 79177tert-Butyl bromoacetate

HCID 205834244-Tert-butyl-3-fluorophenol

Product 1

HCID 58640409tert-Butyl (4-tert-butyl-3-fluorophenoxy)acetateYield 83.2%

Procedure

Sixty % sodium hydride (128 mg, 3.2 mmol), 4-tert-butyl-3-fluorophenol (450 mg, 2.7 mmol), tert-butyl bromoacetate (632 mg, 3.2 mmol) were treated in the same procedure described in Example 3(b) to furnish 634 mg (82% yield) of the title compound as a white solid.

Sources & evidence

ORD record: ord-58454812816f4f95a1c332263622964d
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214824B2

Reaction notes

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