3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid → HCID 54527366, compound

HRID 1776634Notes

Reaction equation

HRID 1776634 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=2[O:15][CH:16]([F:18])[F:17])[C:9](O)=[O:10])[CH2:3][CH2:2]1>C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH2:9][OH:10])[CH:12]=[CH:13][C:14]=2[O:15][CH:16]([F:18])[F:17])[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 23940063-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid

Product 1

HCID 54527366HCID 54527366, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic acid (0.500 g, 1.936 mmol) in anhydrous THF (10 ml), BH3*THF complex (1M solution in THF, 3.87 ml, 3.87 mmol) was added drop wise at RT under nitrogen atmosphere. After 3 hours, the reaction was cooled to 0° C. and quenched with aqueous NH4Cl. The mixture was extracted with EtOAc and the organic phase was dried over Na2SO4 and evaporated under reduced pressure affording (3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)methanol (0.450 g, 1.842 mmol, 95% yield, MS/ESI+ 227.1 [MH−H2O]+). This product was used without any further purification.

Workup

  1. customquenched with aqueous NH4Cl
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialthe organic phase was dried over Na2SO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8c9432b612574a8092376ec5ee8cfbde
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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