Water → 3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehyde

HRID 1776632Notes

Reaction equation

HRID 1776632 reaction equation
[F:1][CH:2]([F:13])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][C:5]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH:22]1[CH2:24][CH2:23]1.O>CN(C=O)C>[CH:22]1([CH2:21][O:12][C:5]2[CH:6]=[C:7]([CH:10]=[CH:11][C:4]=2[O:3][CH:2]([F:13])[F:1])[CH:8]=[O:9])[CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 27582954-(Difluoromethoxy)-3-hydroxybenzaldehyde

Product 1

HCID 189736983-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehydeYield 94.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(difluoromethoxy)-3-hydroxybenzaldehyde (18.4 g, 98 mmol) in DMF (200 ml), potassium carbonate (29.7 g, 215 mmol) and KI (16.3 g, 98 mmol) were added followed by (bromomethyl)cyclopropane (14.28 ml, 148 mmol), and the resulting suspension was stirred at RT for 24 hours. The mixture was poured into water (800 ml) and extracted with diethyl ether (3×300 ml); the combined organic layers were dried over Na2SO4 and the solvent was removed under vacuum affording 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehyde (22.5 g, 93 mmol, 94.8% yield, MS/ESI+ 243.1 [MH]+). This product was used without purification.

Workup

  1. extractionextracted with diethyl ether (3×300 ml)
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-12bef06fb7554cf5a56f500db5336aad
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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