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

HRID 2283165Notes

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].[CH2:14]1[CH2:24][CH2:23]N2C(=NCCC2)C[CH2:15]1.C1(CBr)CC1.O>O1CCCC1>[CH:14]1([CH2:15][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])[CH2:23][CH2:24]1

Participants

Conditions

Temperature: 77.5 °C

Procedure

4-Difluoromethoxy 3-hydroxy benzaldehyde in tetrahydrofuran (5 vol with respect to 4-Difluoromethoxy 3-hydroxy benzaldehyde) was taken in a vessel and DBU (1.5 eq respect to 4-Difluoromethoxy 3-hydroxy benzaldehyde) was added. To this first lot of cyclopropylmethylbromide (1.5 eq respect to 4-Difluoromethoxy 3-hydroxy benzaldehyde) was added and heated to 75-80° C. After 2 hours second lot of cyclopropylmethyl bromide (0.5 eq with respect to 4-Difluoromethoxy 3-hydroxy benzaldehyde) was added and maintained at 75-80° C. for 2 hours. To this third lot of cyclopropylmethyl bromide (0.5 eq with respect to 4-Difluoromethoxy 3-hydroxy benzaldehyde) was added and maintained for 2 hours. The reaction mass was cooled to 20-25° C. and water was added. The reaction mixture was extracted with EtOAc and EtOAc extracts were washed with water. EtOAc was distilled out under reduced pressure at 40° C. to get 3-cyclopropylmethoxy 4-Difluoromethoxy benzaldehyde as brown oil.

Workup

temperaturemaintained at 75-80° C. for 2 hours
temperaturemaintained for 2 hours
temperatureThe reaction mass was cooled to 20-25° C.
extractionThe reaction mixture was extracted with EtOAc and EtOAc extracts
washwere washed with water
distillationEtOAc was distilled out under reduced pressure at 40° C.

Sources & evidence

ORD record: ord-a89a4979bf8a4ceeac5940a3c6fc1ec6
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145365B2

Reaction notes

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