Benzyl 3-Bromopropyl Ether → 3-(3-Benzyloxy-propoxy)-4-fluoro-2-hydroxy-benzaldehyde

HRID 2368009Notes

Reaction equation

HRID 2368009 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([OH:10])[C:3]=1[OH:11].CC([O-])(C)C.[Na+].Br[CH2:19][CH2:20][CH2:21][O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CS(C)=O>[CH2:23]([O:22][CH2:21][CH2:20][CH2:19][O:11][C:3]1[C:4]([OH:10])=[C:5]([CH:8]=[CH:9][C:2]=1[F:1])[CH:6]=[O:7])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 2776064Benzyl 3-Bromopropyl EtherHCID 23676156Sodium t-butoxideHCID 451191034-Fluoro-2,3-dihydroxybenzaldehyde

Product 1

HCID 866647433-(3-Benzyloxy-propoxy)-4-fluoro-2-hydroxy-benzaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Synthesized according to the methods of general procedure 4 in U.S. Pat. Pub. No. 20090227541 (U.S. patent application Ser. No. 12/142,692) using the following reactants and amounts: 4-fluoro-2,3-dihydroxy-benzaldehyde (5.15 g, 32.9 mmol), NaOtBu (6.95 g, 72.3 mmol), DMSO (200 mL), (3-bromo-propoxymethyl)-benzene (8.31 g, 36.3 mmol). Purification: Biotage silica gel chromatography (hexanes/ethyl acetate gradient) generated 4.00 g of a mixture of the title compound and the dialkylated product. This material was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.13 (s, 1H), 7.66-7.54 (m, 5H), 7.53-7.33 (m, 1H), 6.92-6.90 (m, 1H), 4.53 (s, 2H), 4.52-4.44 (m, 2H), 3.71-3.62 (m, 2H), 2.18-2.13 (m, 2H). 19F NMR (376 MHz, DMSO-d6 with D2O) δ (ppm): −121.03-−121.08 (m, 1F).

Workup

  1. customSynthesized
  2. customPurification
  3. customThis material was used in the next step without further purification

Sources & evidence

ORD record
ord-ee24650080f848d6b2cf13ac96ce9a09
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

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