Boron tribromide → 5-Hydroxy-2,3-dihydrobenzofuran-6-carbaldehyde

HRID 1284562Notes

Reaction equation

HRID 1284562 reaction equation
C[O:2][C:3]1[C:4]([CH:12]=[O:13])=[CH:5][C:6]2[O:10][CH2:9][CH2:8][C:7]=2[CH:11]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[C:4]([CH:12]=[O:13])=[CH:5][C:6]2[O:10][CH2:9][CH2:8][C:7]=2[CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 100124745-Methoxy-2,3-dihydrobenzofuran-6-carbaldehyde

Product 1

HCID 135644765-Hydroxy-2,3-dihydrobenzofuran-6-carbaldehydeYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-methoxy-2,3-dihydrobenzofuran-6-carboxaldehyde (24.00 g, 135 mmol) in dry methylene chloride (800 mL) under nitrogen was cooled to an internal temperature of -67°. A solution of boron tribromide (1M in methylene chloride, 63.0 mL 63.0 mmol) was added dropwise. The cooling bath was removed and the mixture allowed to stir for 2.5 hours. The reaction was then quenched by the dropwise addition of methanol (25 mL) and the resulting mixture poured into 10% aqueous sodium chloride (100 mL). The layers were separated and the aqueous layer washed with methylene chloride (2×250 mL), and the combined organic extracts washed with 10% sodium chloride (2×500 mL), dried (Na2SO4), and concentrated. Purification by preparative HPLC (Waters Prep 500, 9:1 hexane:ethyl acetate as eluant) afforded 5-hydroxy-2,3-dihydrobenzofuran-6-carboxaldehyde (16.82 g, 76.1%), m.p. 102-104° C.

Workup

  1. customThe cooling bath was removed
  2. customThe reaction was then quenched by the dropwise addition of methanol (25 mL)
  3. additionthe resulting mixture poured into 10% aqueous sodium chloride (100 mL)
  4. customThe layers were separated
  5. washthe aqueous layer washed with methylene chloride (2×250 mL)
  6. washthe combined organic extracts washed with 10% sodium chloride (2×500 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customPurification by preparative HPLC (Waters Prep 500, 9:1 hexane:ethyl acetate as eluant)

Sources & evidence

ORD record
ord-d92f32401a0b4eb9af6119fed34e2080
Source dataset
uspto-grants-1986_01
Patent number
US04563476

Reaction notes

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