Ammonium Chloride → HCID 17439222, compound

HRID 1836548Notes

Reaction equation

HRID 1836548 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[Br:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][C:10]=1[Br:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 14943384-(Benzyloxy)-3-bromobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 17439222HCID 17439222, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.0 g (3.43 mmol) of 4-(benzyloxy)-3-bromobenzaldehyde [Lit.: R. Baker et al., J. Chem. Soc. Chem. Commun. 14, 1102-1104 (1987)] is initially charged in 10 ml of tetrahydrofuran. At 0° C., 0.04 g (1.03 mmol) of sodium borohydride is added. The reaction mixture is stirred at room temperature for 3 hours. Saturated ammonium chloride solution is then added, and the mixture is extracted twice with ethyl acetate. The combined organic phases are dried with sodium sulphate and the solvent is removed under reduced pressure. This gives 0.98 g (97% of theory) of [4-(benzyloxy)-3-bromophenyl]methanol.

Workup

  1. extractionthe mixture is extracted twice with ethyl acetate
  2. dry with materialThe combined organic phases are dried with sodium sulphate
  3. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-48162d8f9e2b46848f15130d3075ff34
Source dataset
uspto-grants-2004_08
Patent number
US06777442B2

Reaction notes

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