Water → HCID 19261276, compound

HRID 237305Notes

Reaction equation

HRID 237305 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)=[C:6]([CH:9]=1)[CH:7]=[O:8].[BH4-].[Na+].O>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)=[C:6]([CH2:7][OH:8])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 893005HCID 893005, compoundHCID 4311764Sodium borohydride

Product 1

HCID 19261276HCID 19261276, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-bromo-2-(3-chloro-benzyloxy)-benzaldehyde (6.0 g, 18.4 mmol) in MeOH (90 mL) at rt was added NaBH4 (1.07 g, 27.7 mmol) over 1 h. After 18 h at rt, H2O was added (5 mL) and the reaction concentrated to a residual mass, which was dissolved into EtOAc (150 mL). This EtOAc solution was washed with H2O (2×100 mL) and dried to yield the title compound as a light yellow (6.0 g, 100%). MS (ESI): mass calcd. for C14H12BrClO, 327.6; m/z found, 328.3 [M+H]+. 1H NMR (CDCl3) 7.48 (d, J=2.5 Hz, 1H), 7.42-7.20 (m, 5H), 6.76 (d, J=8.7 Hz, 1H), 5.07 (d, J=19.2 Hz, 2H), 4.69 (d, J=17.5 Hz, 2H), 2.15 (t, J=10.0 Hz, 1H).

Workup

  1. concentrationthe reaction concentrated to a residual mass, which
  2. dissolutionwas dissolved into EtOAc (150 mL)
  3. washThis EtOAc solution was washed with H2O (2×100 mL)
  4. customdried

Sources & evidence

ORD record
ord-563812e9949947c39007309eba08c4fb
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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