Sodium borohydride → HCID 59459870, compound

HRID 587781Notes

Reaction equation

HRID 587781 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][OH:11])[CH:5]=[C:6]([Br:9])[C:7]=1[Cl:8].[BH4-].[Na+].BrC1C=C(C=C(Br)C=1Cl)C(OC)=O>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([Br:9])[C:7]=1[Cl:8])[CH:10]=[O:11]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 86722584HCID 86722584, compoundHCID 86722585HCID 86722585, compound

Product 1

HCID 59459870HCID 59459870, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3,5-Dibromo-4-chlorophenyl)methanol: NaBH4 (1.53 g, 40.65 mmol) was added portionwise to a stirred solution of methyl 3,5-dibromo-4-chlorobenzoate (4.45 g, 13.6 mmol) in MeOH (50 mL) at 0° C. The reaction mixture was then stirred at ambient temperature for 8 h. The volatiles were evaporated and the residue was diluted with CH2Cl2 and washed with brine followed by water. The organic layer was dried (Na2SO4), filtered and concentrated to afford the title compound as an off white solid (3.3 g, 80%): 1H NMR (300 MHz, DMSO-d6) δ 7.71 (s, 2H), 5.49 (bs, 1H), 4.48 (d, J=4.5 Hz, 2H); ESIMS m/z 297.9 ([M]+); IR (thin film) 3460, 747, 534 cm−1.

Workup

  1. customThe volatiles were evaporated
  2. additionthe residue was diluted with CH2Cl2
  3. washwashed with brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0a24e09b47654c1e8e2df6facfd5a04e
Source dataset
uspto-grants-2016_01
Patent number
US09226501B2

Reaction notes

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