8-Bromochroman-4-carboxylic acid → (8-bromo-3,4-dihydro-2H-chromen-4-yl)methanol

HRID 2173255Notes

Reaction equation

HRID 2173255 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][CH:7]2[C:12](O)=[O:13]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][CH:7]2[CH2:12][OH:13]

Participants

3

Reactant 1

HCID 675164228-Bromochroman-4-carboxylic acid

Product 1

HCID 67516017(8-bromo-3,4-dihydro-2H-chromen-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 8-bromo-3,4-dihydro-2H-chromene-4-carboxylic acid (3.1 g, 12 mmol) in 50 mL THF was added BH3 (24 mL, 24 mmol, C=1.0 M in THF) dropwise at 0° C. The mixture was stirred at 0° C. for 2-3 hours before quenched with MeOH (8 mL), and evaporated. The residue was partitioned between water and EtOAc. The organic phase was washed with 3N HCl, saturated Na2CO3, and brine, dried over anhydrous Na2SO4 and concentrated to afford (8-bromo-3,4-dihydro-2H-chromen-4-yl)methanol.

Workup

  1. custombefore quenched with MeOH (8 mL)
  2. customevaporated
  3. customThe residue was partitioned between water and EtOAc
  4. washThe organic phase was washed with 3N HCl, saturated Na2CO3, and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-765f330068a042cabb7d7196779be9ac
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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