Phenol → ethyl 6-chloro-7-(phenoxymethyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854978Notes

Reaction equation

[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[C:17]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:18]([C:22]([F:25])([F:24])[F:23])[O:19]2)=[CH:14][C:13]=1[Cl:31]>CN(C=O)C>[Cl:31][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:12]=1[CH2:11][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[O:19][CH:18]([C:22]([F:25])([F:24])[F:23])[C:17]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:16]2

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of phenol (117 mg, 0.69 mmol) in 1 mL DMF was added to a mixture of NaH (30 mg, 0.75 mmol) in 1 mL DMF at 0° C. under argon. After 30 min, a solution of ethyl 7-(bromomethyl)-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate (250 mg, 0.62 mmol) in 2 mL DMF described in Example 157 Step 3 was added dropwise. The reaction was warmed to 25° C. After 18 h, the reaction was filtered through a pad of Celite (1″) and washed with EtOAc (20 mL). The filtrate was concentrated to give a pale yellow solid in 230 mg.

Workup

additionwas added dropwise
waitAfter 18 h
filtrationthe reaction was filtered through a pad of Celite (1″) and
washwashed with EtOAc (20 mL)
concentrationThe filtrate was concentrated
customto give a pale yellow solid in 230 mg

Sources & evidence

ORD record: ord-9ebbc3ee8b3e40f7bcdea67bf48857c8
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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