Boron tribromide → HCID 14239188, compound

HRID 232184Notes

Reaction equation

HRID 232184 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:19]=[CH:18][C:17]2[NH:16][C:15]3[C:14]([CH:20]=[O:21])=[C:13]4[CH:22]=[CH:23][N:24]=[CH:25][C:12]4=[C:11]([CH3:26])[C:10]=3[C:9]=2[CH:8]=1>C(Cl)Cl>[OH:6][C:7]1[CH:19]=[CH:18][C:17]2[NH:16][C:15]3[C:14]([CH:20]=[O:21])=[C:13]4[CH:22]=[CH:23][N:24]=[CH:25][C:12]4=[C:11]([CH3:26])[C:10]=3[C:9]=2[CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 14239186HCID 14239186, compound

Product 1

HCID 14239188HCID 14239188, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 1.6 g (0.6 mL) of boron bromide in 5 mL of dry methylene chloride was added dropwise to a stirred suspension of 200 mg of the methoxyaldehyde 38 in 50 mL of dry CH2Cl2 at -78° C. The stirred suspension was allowed to warm to room temperature and stirred for an additional 6 hours. The mixture was cooled in an ice bath and about 5 mL of ice-water was added after 30 minutes the methylene chloride layer was separated under nitrogen. The aqueous brown suspension was cooled in an ice-bath and made alkaline with 15 mL of 10% sodium hydroxide under nitrogen. The dark red solution was taken to pH 7-8 with the aid of acetic acid, sodium bicarbonate solution. The brown precipitate was collected on a filter, washed with water and dried. The dry solid was triturated with methylene chloride-hexane (1:1) and filtered to give the desired crude phenolic aldehyde. Wt. 170 mg, m.p. 346°-349° C.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. customwas separated under nitrogen
  3. temperatureThe aqueous brown suspension was cooled in an ice-bath
  4. customThe brown precipitate was collected on a filter
  5. washwashed with water
  6. customdried
  7. customThe dry solid was triturated with methylene chloride-hexane (1:1)
  8. filtrationfiltered

Sources & evidence

ORD record
ord-427701c8caf54179b1167433d0a97c7c
Source dataset
uspto-grants-1989_07
Patent number
US04851417

Reaction notes

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